Methanol → HCID 90065574, compound

HRID 522278Notes

Reaction equation

HRID 522278 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C.CO.O>C1COCC1.CCOC(C)=O>[CH:14]1([N:11]2[CH2:10][CH2:9][CH:8]([CH2:7][CH2:6][OH:5])[CH2:13][CH2:12]2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 90065720HCID 90065720, compound

Product 1

HCID 90065574HCID 90065574, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium tetrahydroborate (730 mg) was added to a solution of ethyl(1-cyclopropylpiperidin-4-yl)acetate (2.1 g) in THF (53 mL) under ice-cooling. MeOH (2.4 mL) was added thereto, and the mixture was stirred at room temperature overnight. After water and EtOAc were added to the reaction mixture, the mixture was stirred for 30 minutes, and extraction was performed using EtOAc. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (Hex:EtOAc=80:20 to 60:40), whereby 2-(1-cyclopropylpiperidin-4-yl)ethanol (1.3 g) was obtained as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionextraction
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (Hex:EtOAc=80:20 to 60:40)

Sources & evidence

ORD record
ord-1dfc93c646324398a97a3ee5e0a88048
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

Loading…