Sodium borohydride → HCID 86616461, compound

HRID 226212Notes

Reaction equation

HRID 226212 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[C:9](=[O:12])[CH2:10]Br)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C.C1COCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]([C@H:9]1[CH2:10][O:12]1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57754066HCID 57754066, compound

Product 1

HCID 86616461HCID 86616461, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of (1S)-[3-Bromo-1-(3,4-difluoro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester (0.14 g, 0.36 mmol) in ethanol:THF (2:1) (3 mL) was cooled to 0° C. and treated with sodium borohydride (0.014 g, 0.36 mmol) in one portion. After 30 minutes the cooling bath was removed and the reaction mixture was stirred at ambient temperature for 12 hours. The solvent was removed and the residue partitioned between saturated sodium bicarbonate solution (20 mL) and ethyl acetate (20 mL). The organic phase was washed with saturated sodium bicarbonate solution (25 mL), separated, dried (MgSO4) and the solvent removed at reduced pressure. The product was recrystallized from hexane to give the desired product as the major isomer (>9:1) by NMR (0.095 g, 90%). MS: 300 (M+H, 100%).

Workup

  1. customAfter 30 minutes the cooling bath was removed
  2. customThe solvent was removed
  3. customthe residue partitioned between saturated sodium bicarbonate solution (20 mL) and ethyl acetate (20 mL)
  4. washThe organic phase was washed with saturated sodium bicarbonate solution (25 mL)
  5. customseparated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed at reduced pressure
  8. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-9728535fb1f64353bcefb42c0518cae8
Source dataset
uspto-grants-2009_07
Patent number
US07557137B2

Reaction notes

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