Lithium Chloride → HCID 57446958, compound

HRID 1620970Notes

Reaction equation

HRID 1620970 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18](OC)=[O:19])[CH2:13][C:14]([F:17])([F:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+]>C(O)C.O.Cl>[F:16][C:14]([F:17])([CH3:15])[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:18][OH:19]

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydride2×HCID 57535380HCID 57535380, compound

Product 1

HCID 57446958HCID 57446958, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of methyl N-((benzyloxy)carbonyl)-4,4-difluoro-L-norvalinate (1.59 g, 5.29 mmol) in ethanol (50 mL) was added lithium chloride (919 mg) and the mixture was stirred for 10 minutes. Sodium borohydride (820 mg) was added slowly, the mixture stirred for 2 hours. Then, another portion of sodium borohydride (100 mg) was added and stirring continued for 30 minutes. The mixture was diluted with water (20 mL) and neutralized slowly with 1N HCl followed by the addition of another aliquot of water. The mixture was extracted with ethyl acetate (2×), washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated under vacuum to afford benzyl (1S)-3,3-difluoro-1-(hydroxymethyl)butylcarbamate.

Workup

  1. stirringthe mixture stirred for 2 hours
  2. stirringstirring
  3. waitcontinued for 30 minutes
  4. extractionThe mixture was extracted with ethyl acetate (2×)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-d47187a603764ff3a70c2c3d2ebf7f8f
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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