2,2,2-Trifluoro-1-methoxyethanol → HCID 178461140, compound

HRID 1620971Notes

Reaction equation

HRID 1620971 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH2:16])[CH2:11][C:12]([F:15])([F:14])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:19](O)[C:20]([F:23])([F:22])[F:21]>C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10](/[N:16]=[CH:19]/[C:20]([F:23])([F:22])[F:21])[CH2:11][C:12]([F:15])([F:14])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 57446959HCID 57446959, compound

Product 1

HCID 178461140HCID 178461140, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (2S)-1-((tert-butyl(dimethyl)silyl)oxy)-4,4-difluoropentan-2-amine, from Step 5, and trifluoroacetaldehyde methyl hemiacetal (80%, 0.9 mL) in benzene (20 mL) was refluxed over night with a Dean-Stark apparatus. The solvent was evaporated under vacuum and the residue purified by silica gel chromatography using ethyl acetate and hexanes to afford (2S)-1-((tert-butyl(dimethyl)silyl)oxy)-4,4-difluoro-N-((E)-2,2,2-trifluoroethylidene)pentan-2-amine.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-eae9d76676564b06903d593b27bb9673
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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