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

HRID 660382ノート

反応式

HRID 660382 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-d1b607fa6bc542789d375ffc98b5bd50
出典データセット
uspto-grants-2011_12
特許番号
US08084485B2

反応ノート

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