Water → HCID 60762221, compound

HRID 855286Notes

Reaction equation

HRID 855286 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][N:12]([CH2:19][CH2:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)C(=O)C(F)(F)F)=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].O>C(O)C>[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][NH:12][CH2:19][CH2:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86603039HCID 86603039, compound

Product 1

HCID 60762221HCID 60762221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

102 mg of sodium borohydride (2.7 mmol) were added to a solution of 260 mg of N-(4-tert-butyl-benzyl)-2,2,2-trifluoro-N-[2-(4-methyl-thiazol-2-yl)-ethyl]-acetamide (0.68 mmol) in ethanol at ambient temperature and the reaction mixture was stirred for 3 h. Then water was added and the mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered and the solvent was evaporated. The remaining 195 mg (100%) of (4-tert-butyl-benzyl)-[2-(4-methyl-thiazol-2-yl)-ethyl]-amine were used in the following coupling step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.31 (s, 9H), 2.41 (s, 3H), 3.06 (m, 2H), 3.17 (m, 2H), 3.81 (s, 2H), 6.72 (s, 1H), 7.25 (d, J=8 Hz, 2H), 7.34 (d, J=8 Hz, 2H); MS (ISP) 289.1 (M+H)+.

Workup

  1. extractionthe mixture was extracted three times with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe remaining 195 mg (100%) of (4-tert-butyl-benzyl)-[2-(4-methyl-thiazol-2-yl)-ethyl]-amine were used in the following coupling step without further purification

Sources & evidence

ORD record
ord-29a6b6e0e8954768b44787adc45822d6
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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