Sodium borohydride → HCID 59382972, compound

HRID 451861Notes

Reaction equation

HRID 451861 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:17][CH2:16]1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:22]([O:21][CH:18]1[CH2:17][CH2:16][CH:15]([CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][OH:11])[CH2:20][CH2:19]1)([C:25]([CH3:27])([CH3:28])[CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59383062HCID 59383062, compound

Product 1

HCID 59382972HCID 59382972, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (133 g, 0.32 mol) in 1500 mL methanol was added NaBH4 (73 g, 1.92 mol) at rt. After stirring at rt for 4 h, the solution was evaporated to remove methanol. The remaining solution was treated with water (800 mL), extracted with EtOAc (500 mL×3). The combined organic layers were washed with water (300 mL), dried, filtered, and evaporated to give the desired (S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-hydroxypropan-2-ylcarbamate (102 g, yield 82%). 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. customthe solution was evaporated
  2. customto remove methanol
  3. additionThe remaining solution was treated with water (800 mL)
  4. extractionextracted with EtOAc (500 mL×3)
  5. washThe combined organic layers were washed with water (300 mL)
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a6f075429df948c6b6f4aada61d6309c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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