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【结 构 式】

【分子编号】56141

【品名】(R)-(-)-1-Phenyl-1,2-ethanediol; (R)-(-)-alpha,beta-Dihydroxyethylbenzene; (R)-(-)-Phenyl-1,2-ethanediol; (R)-(-)-Styrene glycol; (-)-Styrene glycol

【CA登记号】16355-00-3

【 分 子 式 】C8H10O2

【 分 子 量 】138.1662

【元素组成】C 69.55% H 7.3% O 23.16%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The reaction of 1(R)-phenylethane-1,2-diol (I) with N-hydroxyphthalimide (II) by means of DEAD and PPh3 gives the N-alcoxyphthalimide (III) with(S)-configuration. The hydrazinolysis of (III) with hydrazine hydrate affords the O-alkylhydroxylamine (IV), which is condensed with benzaldehyde (V) to provide the alkylated benzaldoxime (VI). The alkylation of the oxime (VI) with vinyl lithium (VII) in toluene gives the N, O dialkylated hydroxylamine (VIII), which is treated with Zn and AcOH to yield 1(R)-phenylallylamine (IX). The protection of the amine (IX) with Boc2O and NaOH affords the carbamate (X), which is oxidized at the vinyl double bond by means of OsO4 and NaIO4 to provide the acetaldehyde (XI). The reaction of aldehyde (XI) with allylmagnesium bromide (XII) in ethyl ether gives the aminoalcohol (XIII), which is protected with Tbdms-Cl and imidazole to yield the silyl ether (XIV).

1 Yamazaki, N.; et al.; Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)ethylamines and application to a synthesis of calcimimetics (+)-NPS R-568 and its thio analogue. Tetrahedron Lett 2001, 42, 30, 5029.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 56141 (R)-(-)-1-Phenyl-1,2-ethanediol; (R)-(-)-alpha,beta-Dihydroxyethylbenzene; (R)-(-)-Phenyl-1,2-ethanediol; (R)-(-)-Styrene glycol; (-)-Styrene glycol 16355-00-3 C8H10O2 详情 详情
(II) 13505 N-Hydroxyphthalimide; 2-Hydroxy-1H-isoindole-1,3(2H)-dione 524-38-9 C8H5NO3 详情 详情
(III) 56142 2-{[(1S)-2-hydroxy-1-phenylethyl]oxy}-1H-isoindole-1,3(2H)-dione C16H13NO4 详情 详情
(IV) 56143 (2S)-2-(aminooxy)-2-phenyl-1-ethanol C8H11NO2 详情 详情
(V) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(VI) 62256 benzaldehyde O-[(1S)-2-hydroxy-1-phenylethyl]oxime C15H15NO2 详情 详情
(VII) 42368 vinyllithium 917-57-7 C2H3Li 详情 详情
(VIII) 62257 (2S)-2-phenyl-2-({[(1R)-1-phenyl-2-propenyl]amino}oxy)-1-ethanol C17H19NO2 详情 详情
(IX) 62258 (1R)-1-phenyl-2-propenylamine; (1R)-1-phenyl-2-propen-1-amine C9H11N 详情 详情
(X) 62259 tert-butyl (1R)-1-phenyl-2-propenylcarbamate C14H19NO2 详情 详情
(XI) 45428 tert-butyl (1S)-2-oxo-1-phenylethylcarbamate C13H17NO3 详情 详情
(XII) 61128   C4H8 详情 详情
(XIII) 62260 tert-butyl (1S)-2-hydroxy-1-phenyl-4-pentenylcarbamate C16H23NO3 详情 详情
(XIV) 62261 tert-butyl (1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-4-pentenylcarbamate C22H37NO3Si 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

A new procedure for the asymmetric synthesis of amine (III) was reported. Mitsunobu coupling of N-hydroxyphthalimide (V) with the chiral auxiliary (R)-phenylglycol (IV) yielded the (S)-alkoxyphthalimide (VI). Hydrazinolysis of (VI) provided the free alkoxyamine (VII), which was condensed with 3-methoxybenzaldehyde (VIII) to afford oxime (IX). Diastereoselective addition of methyllithium to the oxime ether (IX) led to the methyl adduct (X) as the major isomer. Then, reductive N-O bond cleavage to furnish amine (III) was carried out by using zinc-acetic acid or, with an improved yield, using molybdenum hexacarbonyl.

1 Yamazaki, N.; et al.; Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)ethylamines and application to a synthesis of calcimimetics (+)-NPS R-568 and its thio analogue. Tetrahedron Lett 2001, 42, 30, 5029.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 56140 (R)-1-(3-Methoxyphenyl)ethylamine; (R)-3-Methoxy-alpha-methylbenzylamine; (R)-m-Methoxy-alpha-methylbenzylamine 88196-70-7 C9H13NO 详情 详情
(IV) 56141 (R)-(-)-1-Phenyl-1,2-ethanediol; (R)-(-)-alpha,beta-Dihydroxyethylbenzene; (R)-(-)-Phenyl-1,2-ethanediol; (R)-(-)-Styrene glycol; (-)-Styrene glycol 16355-00-3 C8H10O2 详情 详情
(V) 13505 N-Hydroxyphthalimide; 2-Hydroxy-1H-isoindole-1,3(2H)-dione 524-38-9 C8H5NO3 详情 详情
(VI) 56142 2-{[(1S)-2-hydroxy-1-phenylethyl]oxy}-1H-isoindole-1,3(2H)-dione C16H13NO4 详情 详情
(VII) 56143 (2S)-2-(aminooxy)-2-phenyl-1-ethanol C8H11NO2 详情 详情
(VIII) 20589 3-methoxybenzaldehyde; m-Anisaldehyde 591-31-1 C8H8O2 详情 详情
(IX) 56144 3-methoxybenzaldehyde O-[(1S)-2-hydroxy-1-phenylethyl]oxime C16H17NO3 详情 详情
(X) 56145 (2S)-2-({[(1R)-1-(3-methoxyphenyl)ethyl]amino}oxy)-2-phenyl-1-ethanol C17H21NO3 详情 详情
Extended Information