• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】64504

【品名】tert-butyl allyl[(1S,2S)-2-hydroxy-1-phenyl-3-butenyl]carbamate

【CA登记号】

【 分 子 式 】C18H25NO3

【 分 子 量 】303.40144

【元素组成】C 71.26% H 8.31% N 4.62% O 15.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

The esterification of L-phenylglycine (I) with AcCl and methanol gives the methyl ester (II), which is N-protected by means of Boc2O and TEA to yield the N-Boc derivative (III). The reduction of (III) with NaBH4 in ethanol/THF affords the alcohol (IV), which is oxidized by means of (COCl)2 and DMSO to provide the carbaldehyde (V). The reaction of (V) with vinylmagnesium bromide (VI) in THF gives the allyl alcohol (VII), which is protected with Tbdms-Cl and imidazole to yield the silyl ether (VIII). The alkylation of (VIII) with allyl bromide (IX) and NaH in DMF affords the N-allyl derivative (X), which is desilylated by means of TBAF and AcOH in THF to provide the allyl alcohol (XI). The ring closing metathesis reaction of (XI) with a Grubbs' catalyst in dichloromethane gives the tetrahydropyridine (XII), which is treated with H2 over Pd/C in ethanol to yield the chiral protected piperidine (XIII). The condensation of (XIII) with 3,5-bis(trifluoromethyl)benzyl bromide (XIV) by means of NaH in DMF affords the benzyl ether (XV), which is finally deprotected with TFA to provide the target piperidine.

1 Bhaskar, G.; Rao, B.V.; Stereoselective synthesis of L-733,060. Tetrahedron Lett 2003, 44, 5, 915.
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) 10716 (2S)-2-Amino-2-phenylethanoic acid; L-(+)-alpha-Phenylglycine 2935-35-5 C8H9NO2 详情 详情
(II) 10717 methyl (2S)-2-amino-2-phenylethanoate C9H11NO2 详情 详情
(III) 12485 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoate C14H19NO4 详情 详情
(IV) 59225 (R)-N-(tert-Butoxycarbonyl)-phenylglycinol; N-t-BOC-D-phenylglycinol 102089-74-7 C13H19NO3 详情 详情
(V) 45428 tert-butyl (1S)-2-oxo-1-phenylethylcarbamate C13H17NO3 详情 详情
(VI) 16524 bromo(vinyl)magnesium 1826-67-1 C2H3BrMg 详情 详情
(VII) 64501 tert-butyl (1S,2S)-2-hydroxy-1-phenyl-3-butenylcarbamate C15H21NO3 详情 详情
(VIII) 64502 tert-butyl (1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-3-butenylcarbamate C21H35NO3Si 详情 详情
(IX) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(X) 64503 tert-butyl allyl((1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenyl-3-butenyl)carbamate C24H39NO3Si 详情 详情
(XI) 64504 tert-butyl allyl[(1S,2S)-2-hydroxy-1-phenyl-3-butenyl]carbamate C18H25NO3 详情 详情
(XII) 64505 tert-butyl (2S,3S)-3-hydroxy-2-phenyl-3,6-dihydro-1(2H)-pyridinecarboxylate C16H21NO3 详情 详情
(XIII) 64499 tert-butyl (2S,3S)-3-hydroxy-2-phenyl-1-piperidinecarboxylate C16H23NO3 详情 详情
(XIV) 27677 1-(bromomethyl)-3,5-bis(trifluoromethyl)benzene 32247-96-4 C9H5BrF6 详情 详情
(XV) 64500 tert-butyl (2S,3S)-3-{[3,5-bis(trifluoromethyl)benzyl]oxy}-2-phenyl-1-piperidinecarboxylate C25H27F6NO3 详情 详情
Extended Information