Sodium borohydride → HCID 59383050, compound

HRID 1254206Notes

Reaction equation

HRID 1254206 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17][CH2:16]1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[F:21][C:18]1([F:22])[CH2:17][CH2:16][CH:15]([CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][OH:11])[CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59382883HCID 59382883, compound

Product 1

HCID 59383050HCID 59383050, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4,4-difluorocyclohexyl)propanoate (28.6 g, 0.089 mol), prepared as described in U.S. Pat. No. 5,688,946, in ethanol (600 mL) at 0° C. was added NaBH4 (27.1 g, 0.713 mol) in portions while the temp. was maintained at 0-5° C. The mixture was stirred for 2-3 h at rt and then evaporated. The residue was partitioned between water and EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4 and evaporated to give (S)-tert-butyl 1-(4,4-difluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (25.7 g, 99%), which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): 4.61 (d, J=7.6 Hz, 1H), 3.70 (m, 1H), 3.50 (m, 1H), 2.45-1.10 (m, 11H), 1.44 (s, 9H); MS (E/Z): 295 (M+H+).

Workup

  1. customevaporated
  2. customThe residue was partitioned between water and EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-643c833dd1244f04ad2b28cc646794fd
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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