Sodium borohydride → HCID 59383050, compound

HRID 451809Notes

Reaction equation

HRID 451809 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+]>CCO>[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) in EtOH (600 mL) at 0° C. was added NaBH4 (27.1 g, 0.713 mol) in portions while the temperature was maintained at 0-5° C. The mixture was stirred for 2-3 hr 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 (CDCl3, 400 MHz) δ 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 ESI +ve m/z 295 (M+1).

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-bb8a5cbe39044ecf9f616b29264feeb3
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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