Sodium triacetoxyborohydride → HCID 86650221, compound

HRID 1047378Notes

Reaction equation

HRID 1047378 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].[C:17]([Si:21]([CH3:31])([CH3:30])[O:22][CH:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:17]([Si:21]([CH3:31])([CH3:30])[O:22][CH:23]1[CH2:28][CH2:27][CH:26]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:15])([F:16])[F:1])=[C:5]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[CH2:25][CH2:24]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 106094304-(tert-Butyldimethylsilyloxy)cyclohexanoneHCID 136485245-Amino-2-(trifluoromethoxy)benzotrifluoride

Product 1

HCID 86650221HCID 86650221, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(4-Trifluoromethoxy-3-trifluoromethyl-phenyl)-amine (735 mg, 3 mmol) and 4-(tert-butyl-dimethyl-silyloxy)-cyclohexanone (685 mg, 3 mmol) were dissolved in dichloromethane (25 mL). Next, sodium triacetoxyborohydride (1.27 g, 6 mmol) was added. The resulting mixture was stirred at room temperature for 6 days. Afterward, the mixture was diluted with dichloromethane (25 mL), washed with water (20 mL), washed with HCl 1N (20 mL), washed with water (20 mL), and washed with brine (20 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum to afford an oily residue. The residue was purified by column chromatography on silica gel (pentane/ether gradient). The desired product was isolated as a colorless oil (900 mg of 1:1 mixtures of cis and trans isomers, 66% yield).

Workup

  1. washwashed with water (20 mL)
  2. washwashed with HCl 1N (20 mL)
  3. washwashed with water (20 mL)
  4. washwashed with brine (20 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto afford an oily residue
  10. customThe residue was purified by column chromatography on silica gel (pentane/ether gradient)

Sources & evidence

ORD record
ord-58604a9a892c46b988d8c880e38016b0
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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