Sodium triacetoxyborohydride → HCID 89554966, compound

HRID 922783Notes

Reaction equation

HRID 922783 reaction equation
O=[CH:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[NH2:13][CH:14]([C:17]([F:20])([F:19])[F:18])[CH2:15][OH:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:18][C:17]([F:20])([F:19])[CH:14]([NH:13][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])[CH2:15][OH:16]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamateHCID 22385729HCID 22385729, compound

Product 1

HCID 89554966HCID 89554966, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (S)-tert-butyl (1-oxopropan-2-yl)carbamate (3.15 g, 18.18 mmol), and DCM (91 ml) was added 2-amino-3,3,3-trifluoropropan-1-ol (2.230 g, 17.28 mmol). Stirred at ambient temperature for 10 minutes and then added sodium triacetoxyborohydride (5.78 g, 27.3 mmol). The mixture was stirred overnight. The reaction was diluted with DCM and then washed with 1 N NaOH, brine dried over MgSO4, filtered and the solvent removed to provide 4.0 grams of tert-butyl ((2S)-1-((1,1,1-trifluoro-3-hydroxypropan-2-yl)amino)propan-2-yl)carbamate as a colorless oil that was used without further purification. LRMS m/z (M+H)+ 287.3 found, 287.3 required.

Workup

  1. stirringThe mixture was stirred overnight
  2. washwashed with 1 N NaOH, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-8863df7dc13c430faa86983c617c9c37
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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