Sodium borohydride → HCID 40573861, compound

HRID 878402Notes

Reaction equation

HRID 878402 reaction equation
[CH2:1]([O:8][C:9](/[N:11]=[C:12](/[C:18]([F:21])([F:20])[F:19])\[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([F:19])([F:20])[F:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 5706450HCID 5706450, compound

Product 1

HCID 40573861HCID 40573861, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl (2E)-2-{[(benzyloxy)carbonyl]imino}-3,3,3-trifluoropropanoate (2500 g, 8.25 mol) in diethyl ether (15 L) under a nitrogen atmosphere was added sodium borohydride (627 g, 16.5 mol) in several batches at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, the reaction mixture was quenched with water (500 mL) and extracted with ethyl acetate (3×2000 mL). The organic layers were combined, washed with brine (2×500 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether) to afford ethyl N-[(benzyloxy)carbonyl]-3,3,3-trifluoroalaninate.

Workup

  1. customthe reaction mixture was quenched with water (500 mL)
  2. extractionextracted with ethyl acetate (3×2000 mL)
  3. washwashed with brine (2×500 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via chromatography on silica gel (10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-21d2a70070914c12a623ac60fd122355
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

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