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

HRID 660382Notes

Reaction equation

HRID 660382 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-d1b607fa6bc542789d375ffc98b5bd50
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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