Sodium borohydride → tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

HRID 660382노트

반응식

HRID 660382 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13](OCC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 53806764(2S,4S)-ethyl 4-(benzyloxymethyl)-2-(tert-butoxycarbonylamino)-5-methylhexanoate

생성물 1

HCID 70642503tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate수율 97.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of (2S,4S)-ethyl 4-(benzyloxymethyl)-2-(tert-butoxycarbonylamino)-5-methylhexanoate (16 g, 42.2 mmol) in EtOH (200 mL) at rt was added NaBH4 (12.8 g, 0.338 mol) in portions. The mixture was stirred for 16 h. The solvent was evaporated and the residue was partitioned between H2O (300 mL) and EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried over MgSO4 and evaporated to give tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate (14.4 g, 97%). 1H NMR (400 MHz, CDCl3): δ7.35-7.29 (m, 5H), 4.95 (brs, 1H), 4.50 (s, 2H), 3.62 (brs, 3H), 3.50 (m, 1H), 3.35 (m, 1H), 1.75 (m, 1H), 1.54-1.45 (m, 3H), 1.43 (s, 9H), 0.88 (m, 6H); MS: 352 (M++1)

후처리

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between H2O (300 mL) and EtOAc (3×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-d1b607fa6bc542789d375ffc98b5bd50
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084485B2

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