Lithium borohydride → Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

HRID 1504838노트

반응식

HRID 1504838 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1.[Cl-].[NH4+]>[OH:15][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11][S:12][CH3:13]

참가 물질

5

반응물 2

HCID 4148881Lithium borohydrideHCID 11097398(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoate

생성물 1

HCID 11356792Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

To a solution of methyl N-(tert-butoxycarbonyl)methioninate (47.7 g, 0.181 mol) in THF (500 mL) was added lithium borohydride (16.0 g, 0.734 mol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 2 hours, the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H22NO3S [M+H]+ 236. found 236. 1H NMR (400 MHz, CD3OD) δ 3.68-3.64 (m, 1H), 3.54-3.47 (m, 2H), 2.59-2.48 (m, 2H), 2.10 (s, 3H), 1.88-1.64 (m, 2H), 1.49 (s, 9H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-55297eb4a0e54e548b67bcb026d6c517
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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