4-(Trifluoromethyl)piperidine → HCID 69663224, compound

HRID 2212085Notes

Reaction equation

HRID 2212085 reaction equation
C([BH3-])#N.[Na+].[C:5]1([S:11]([CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]=O)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:21][C:22]([F:30])([F:29])[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CO>[C:5]1([S:11]([CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][N:26]2[CH2:27][CH2:28][CH:23]([C:22]([F:30])([F:29])[F:21])[CH2:24][CH2:25]2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1364694-(Trifluoromethyl)piperidineHCID 5003444Sodium cyanoborohydrideHCID 86760233HCID 86760233, compound

Product 1

HCID 69663224HCID 69663224, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (78 mg, 1.2 mmol) was added to a stirred solution of the crude 4-benzenesulfonyl-3,3-dimethyl-butyraldehyde (240 mg, 1 mmol) and 4-trifluoromethylpiperidine (321 mg, 2.1 mmol) in methanol (4 ml). The mixture was stirred for 1 hour, quenched with sat. aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (dichloromethane:methanol) to give the title product.

Workup

  1. customquenched with sat. aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified on silica (dichloromethane:methanol)

Sources & evidence

ORD record
ord-69a716a476164dcd972e69702f02b6a6
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

Loading…