Benzyl Alcohol → Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate

HRID 1695952Notes

Reaction equation

HRID 1695952 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:10]=1)=[O:2].C(O)C1C=CC=CC=1>[Pd].CCOC(C)=O>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 57774423HCID 57774423, compound

Product 1

HCID 57774474Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylateYield 139.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(2-formylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (305 mg, 1.06 mmol, 1 eq.)), 5% Pd/C (30 mg) and EtOAc (10 mL) was stirred at room under 1 atm of H2 for 18 h. Mainly benzyl alcohol was observed by LC/MS and HPLC (Rt=4.21 min). The catalyst was filtered off, the filtrate was concentrated in vacuo, and purified by ISCO chromatography (24 g, Si35, 10 to 25% EtOAC in Hexanes, Rf˜0.6 in 1:1 Hex:EtOAc, to give 432 mg (52%) of tert-butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate as a thick, colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by ISCO chromatography (24 g, Si35, 10 to 25% EtOAC in Hexanes

Sources & evidence

ORD record
ord-26254319988b45e6b59a29db92e1b0d0
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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