Sodium borohydride → HCID 21902127, compound

HRID 1398457Notes

Reaction equation

HRID 1398457 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][CH:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])[C:10](OCC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[F:18][C:17]([F:19])([F:20])[CH:16]([CH3:21])[CH2:15][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86710432Ethyl 2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoro-4-methylpentanoate

Product 1

HCID 21902127HCID 21902127, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of ethyl 2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoro-4-methylpentanoate (500 mg, 1.596 mmol) in ethanol (2 mL) at 0° C. was added NaBH4 (604 mg, 15.96 mmol). The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was quenched with aqueous ammonia. The solution was filter through a glass funnel and the resulting filtrate was concentrated to afford the tert-butyl (5,5,5-trifluoro-1-hydroxy-4-methylpentan-2-yl)carbamate (400 mg, 1.475 mmol, 92% crude yield) as a colorless gummy semisolid material. The material was carried on without further purification. LC/MS (ESI) m/e 172.1 [(M+H)+, calcd for C6H13F3NO 172.1] LC/MS retention time (Method A): tR=2.1 min.

Workup

  1. customThe reaction mixture was quenched with aqueous ammonia
  2. filtrationThe solution was filter through a glass funnel
  3. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-573503334a7648d09ed40e6422251a91
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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