Lithium borohydride → HCID 57454785, compound

HRID 1880527Notes

Reaction equation

HRID 1880527 reaction equation
C[O:2][C:3](=O)[C@@H:4]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8].[Li+].[BH4-]>C1COCC1>[CH2:15]([O:14][C:12](=[O:13])[NH:11][C@H:4]([CH2:3][OH:2])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67298331HCID 67298331, compound

Product 1

HCID 57454785HCID 57454785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S)-2-Benzyloxycarbonylamino-5,5,5-trifluoropentanoic acid methyl ester from Step 2 was dissolved in dry THF (400 mL). A solution of LiBH4 (2.11 g in 100 mL of dry THF) was added dropwise with stirring and the solution was allowed to stir at ambient temperature overnight. The reaction mixture was concentrated by rotary evaporation and 400 mL of water was added. The pH was then adjusted to pH 2 by addition of concentrated HCl and then the product was extracted into ethyl acetate. The organic phase was washed two times with water, dried with MgSO4, filtered, and concentrated by rotary evaporation to yield crude (S)-(4,4,4-trifluoro-1-hydroxymethyl-butyl)-carbamic acid benzyl ester.

Workup

  1. stirringto stir at ambient temperature overnight
  2. concentrationThe reaction mixture was concentrated by rotary evaporation and 400 mL of water
  3. additionwas added
  4. additionThe pH was then adjusted to pH 2 by addition of concentrated HCl
  5. extractionthe product was extracted into ethyl acetate
  6. washThe organic phase was washed two times with water
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-0d13469b52f94680a4121b99139f1d27
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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