Lithium borohydride → (R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

HRID 1450741노트

반응식

HRID 1450741 반응식
C[O:2][C:3]([C@@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O.[BH4-].[Li+]>CCOCC>[CH3:11][C:7]1([CH3:10])[N:6]([C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C@H:5]([CH2:3][OH:2])[CH2:9][O:8]1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 53934458(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxylic Acid Methyl Ester

생성물 1

HCID 54137581(R)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 h at reflux and 18 h at room temperature. The resulting mixture is diluted with ether and quenched with methanol. The volatiles are removed and the residue is taken up in EtOAc/H2O. Workup provides the crude alcohol which is purified by chromatography (2:1 hexane/EtOAc): NMR δ0.88 (m, 3H), 1.30 (m, 6H), 1.54 (s, 3H), 1.62 (s, 3H), 2.35 (m, 2H), 3.30-4.40 (complex m, 6H); MS (HR-E1) m/z 243.1837 (M calcd. for C13H25NO3 243.1840); [α]D26 =-5±1 (CHCl3).

후처리

  1. customquenched with methanol
  2. customThe volatiles are removed

출처 및 근거

ORD 기록
ord-66daa9755dae42ffaefc422a20dd1a7a
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602275

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