4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate

HRID 238284Notes

Reaction equation

HRID 238284 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](OC)=[O:27])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1.C(OCC)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][OH:27])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 111629634-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 57774474Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylateYield 63.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (0.026 g, 0.7 mmol) was suspended in dry THF (1 mL) under a nitrogen atmosphere and cooled in an ice bath. A solution of 4-(2-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.27 g, 0.7 mmol) in dry THF (2 mL) was added drop wise and the reaction mixture stirred for 1 hour. The reaction mixture was diluted with diethyl ether (5 mL) and quenched with hydrochloric acid (1 N, 5 mL). The organic solution was separated and washed with saturated aqueous sodium hydrogen carbonate (5 mL) and brine (5 mL), dried over magnesium sulphate, filtered and the solvent removed under vacuum to give the title compound as a colourless gum (0.13 g). LCMS m/z 292.0 [M+H]+. R.T.=4.57 min (Analytical Method 4).

Workup

  1. temperaturecooled in an ice bath
  2. customquenched with hydrochloric acid (1 N, 5 mL)
  3. customThe organic solution was separated
  4. washwashed with saturated aqueous sodium hydrogen carbonate (5 mL) and brine (5 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-50c532e69923486da2c92a5aafb588e6
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

Loading…