Sodium borohydride → HCID 59382972, compound

HRID 2355467Notes

Reaction equation

HRID 2355467 reaction equation
C[O:2][C:3]([C@@H:5]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][CH2:8]1)=O.[BH4-].[Na+]>CCO>[C:24]([O:23][C:22]([NH:21][C@@H:5]([CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH2:11][CH2:12]1)[CH2:3][OH:2])=[O:28])([CH3:26])([CH3:25])[CH3:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59383062HCID 59383062, compound

Product 1

HCID 59382972HCID 59382972, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (S)-1-(methoxycarbonyl)-2-(4-(t-butyldimethylsilyloxy)-cyclohexyl)ethylcarbamate (25 g, 60 mmol) in EtOH (500 mL) at 0° C. was added NaBH4 (18 g, 480 mmol) in portions. The mixture was stirred for 6 h at rt and then evaporated. The residue was partitioned between water (200 mL) and EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, and evaporated to give (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethylsilyloxy)cyclohexyl)propan-1-ol (23 g, yield 98%). 1H NMR (CDCl3, 400 MHz) δ 0.08 (d, 6H), 0.89 (d, 9H), 1.30 (m, 4H), 1.40 (t, 2H), 1.45 (s, 9H), 1.61 (m, 1H), 1.58 (m, 1H), 1.68 (t, 4H), 1.85 (d, 1H) 3.50 (m, 1H), 3.65 (m, 1H), 3.73 (m, 1H), 3.91 (s, 1H), 4.53 (s, 1H).

Workup

  1. customevaporated
  2. customThe residue was partitioned between water (200 mL) and EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ed7954e63fac4fe2847febb83c0f8d37
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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