Sodium borohydride → HCID 23237021, compound

HRID 878403Notes

Reaction equation

HRID 878403 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH2:6]([O:13][C:14]([NH:16][C@H:17]([C:22](OCC)=[O:23])[C:18]([F:21])([F:20])[F:19])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[F:19][C:18]([F:20])([F:21])[CH:17]([NH:16][C:14](=[O:15])[O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:22][OH:23]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 40573861HCID 40573861, compound

Product 1

HCID 23237021HCID 23237021, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of calcium chloride (2885 g, 26.23 mol) in diethyl ether (8 L) under a nitrogen atmosphere was added sodium borohydride (1993 g, 52.45 mol). To this mixture was added dropwise ethyl N-[(benzyloxy)carbonyl]-3,3,3-trifluoroalaninate (3.28 M solution in diethyl ether, 2000 mL, 6.56 mol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 16 hours, reaction mixture was quenched with water (10 L) 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 benzyl (1,1,1-trifluoro-3-hydroxypropan-2-yl)carbamate.

Workup

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

Sources & evidence

ORD record
ord-65950fd58d3c4a74a57432737fe65b0f
Source dataset
uspto-grants-2015_03
Patent number
US08987456B2

Reaction notes

Loading…