Water → 1-(Cyclopropylmethyl)piperidin-4-ol

HRID 901101

Reaction equation

HRID 901101 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[BH4-].[Na+].O.[OH-].[Na+]>C(O)C.ClCCl>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 180021811-(Cyclopropylmethyl)piperidin-4-one

Product 1

HCID 214287521-(Cyclopropylmethyl)piperidin-4-olYield 51.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 1-cyclopropylmethyl-piperidin-4-one (314 mg, 2 mmol, 1.0 eq.) in ethanol (4 mL) was added sodium borohydride (61 mg, 2 mmol, 0.75 eq.). The reaction mixture was stirred 16 h at room temperature. Water, sodium hydroxide and dichloromethane were added and the reaction mixture was stirred 2 h at room temperature. The aqueous layer was extracted with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered then concentrated to dryness in vacuo to yield 160 mg (50%) of the tide compound as colorless oil, witch was used in the next step without further purification. MS (m/e): 156.3 (MH+, 100%).

Workup

  1. stirringthe reaction mixture was stirred 2 h at room temperature
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthen concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-e5dc8ef68c4e4b3b899fcdc442eaa797
Source dataset
uspto-grants-2008_04
Patent number
US07361682B2

Linked notes

Loading…