Sodium borohydride → (2S)-2-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester

HRID 602925노트

반응식

HRID 602925 반응식
[C:1]([O:5][C:6](=[O:20])[C@@H:7]([N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6](=[O:20])[C@@H:7]([N:9]1[C:10](=[O:19])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]1[OH:18])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 13005797(2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester

생성물 1

HCID 66650196(2S)-2-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester수율 66.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid tert-butyl ester (426 mg, 1.55 mmol) in a mixture of THF (10 mL) and MeOH (2 mL) was added sodium borohydride (181 mg, 4.8 mmol) in one portion. The reaction mixture was stirred for 30 minutes before solvents were evaporated at room temperature and the residue was columned on silica (Petrol/AcOEt, 8/2) to afford the sub-title compound as colorless oil (284 mg, 66%): 1H NMR (400 MHz CDCl3) δ 1.38-1.40 (9H, 2s), 1.57-1.60 (3H, 2d), 4.38-4.45 (1H, m), 4.65-4.76 (1H, m), 5.81-6.01 (1H, 2d), 7.33-7.64 (4H, d).

후처리

  1. customwere evaporated at room temperature

출처 및 근거

ORD 기록
ord-43d3a499076947a08e9f01e6b9925fad
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906650B2

반응 노트

불러오는 중…