Lithium Chloride → HCID 57446951, compound

HRID 1880523Notes

Reaction equation

HRID 1880523 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20](OC)=[O:21])[CH2:13][C@@H:14]([C:16]([F:19])([F:18])[F:17])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[Cl-].[BH4-].[Na+]>CCO>[F:17][C:16]([F:18])([F:19])[C@@H:14]([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)[CH2:20][OH:21]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 59021655HCID 59021655, compound

Product 1

HCID 57446951HCID 57446951, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl (4S)—N-[(benzyloxy)carbonyl]-5,5,5-trifluoro-L-leucinate (5.4 g, 16.2 mmol) in EtOH (150 mL) at room temperature was added LiCl (2.8 g, 66 mol) and the mixture was stirred for 10 to 15 min, followed by the addition of NaBH4 (2.5 g, 66 mmol). The mixture was stirred at room temperature for 6 h. After dilution with H2O (60 mL), the mixture was quenched with 6M aqueous HCl (18 mL). More H2O was added and the mixture was extracted with EtOAc (2×). The combined EtOAc extracts were washed with brine, dried (Na2SO4) and concentrated to give the crude benzyl (1S,3S)-4,4,4-trifluoro-1-(hydroxymethyl)-3-methylbutylcarbamate.

Workup

  1. stirringThe mixture was stirred at room temperature for 6 h
  2. customAfter dilution with H2O (60 mL), the mixture was quenched with 6M aqueous HCl (18 mL)
  3. additionMore H2O was added
  4. extractionthe mixture was extracted with EtOAc (2×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-92ba7e06ea7443fdbb2b1a12262f630a
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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