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

【结 构 式】

【分子编号】55688

【品名】[(5S)-3-isopropyl-2-phenyl-1,3-oxazolidin-5-yl]methanol

【CA登记号】

【 分 子 式 】C13H19NO2

【 分 子 量 】221.2994

【元素组成】C 70.56% H 8.65% N 6.33% O 14.46%

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:(VII)

The 3-(isopropylamino)propane-1,2(S)-diol (IV) intermediate has been obtained by two different methods: 1. The oxidation of 1,2,5,6-O-diisopropylidene-D-mannitol (I) with Pb(OAc)4 in THF gives (R)-2,3-O-isopropylideglyceraldehyde (II), which is reductocondensed with isopropylamine by means of H2 over Pd/C in methanol to yield (S)-3-(isopropylamino)-1,2-O-isopropylidenepropane-1,2-diol (III). The cleavage of the isopropylidene protecting group of (III) in hot 6N HCl affords the desired 3-(isopropylamino)propane-1,2-diol (IV) intermediate. 2. The reductocondensation of (R)-glyceraldehyde (V) with isopropylamine by means of H2 over Pd/C in methanol gives the desired 3-(isopropylamino)propane-1,2-diol (IV) intermediate. The cyclization of (IV) with benzaldehyde (VI) by heating at 150 C gives the oxazolidine (VII), which is treated with Ts-Cl and K2CO3 in pyridine to yield the tosylate (VIII). Finally, this compound is condensed with 4-[2-(cyclopropylmethoxy)ethyl]phenol (IX) by means of NaH in DMF and hydrolyzed with conc. aq. HCl to provide the target isopropanol derivative.

1 Baldwin, J.J.; et al.; J Med Chem 1979, 22, 11, 1284.
2 Weinstock, L.M.; et al.; J Org Chem 1976, 41, 19, 3121.
3 Manoury, P.; Binet, J. (Sanofi-Synthelabo); S isomer of betaxolol, its preparation and its application in therapy. GB 2130585 .
4 Manoury, P.M.; et al.; Synthesis of a series of compounds related to betaxolol, a new beta1-adrenoceptor antagonist with a pharmacological and pharmacokinetic profile optimized for the treatment of chronic cardiovascular diseases. J Med Chem 1987, 30, 6, 1003-11.
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) 45944 (1S,2S)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-ethanediol 1707-77-3 C12H22O6 详情 详情
(II) 36759 (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 15186-48-8 C6H10O3 详情 详情
(III) 55685 N-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-N-isopropylamine; N-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-2-propanamine C9H19NO2 详情 详情
(IV) 55687 (2S)-3-(isopropylamino)-1,2-propanediol C6H15NO2 详情 详情
(V) 55686 (R)-(+)-2,3-Dihydroxypropanal; D-(+)-Glyceraldehyde; D-Glyceraldehyde 453-17-8 C3H6O3 详情 详情
(VI) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(VII) 55688 [(5S)-3-isopropyl-2-phenyl-1,3-oxazolidin-5-yl]methanol C13H19NO2 详情 详情
(VIII) 55689 [(5S)-3-isopropyl-2-phenyl-1,3-oxazolidin-5-yl]methyl 4-methylbenzenesulfonate C20H25NO4S 详情 详情
(IX) 33330 4-[2-(Cyclopropylmethoxy)ethyl]phenol; p-(Cyclopropylmethoxyethyl)phenol C12H16O2 详情 详情
Extended Information