Benzyl chloroformate → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 397677Notes

Reaction equation

HRID 397677 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[OH:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.C(N(C(C)C)C(C)C)C>ClCCl>[OH:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:15]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl chloroformate (7.88 ml) was added over ten minutes to an ice-cold solution of 3-hydroxymethyl piperidine (5.76 g) and ethyldiisopropylamine (9.58 ml) in dichloromethane (300 ml). The reaction mixture was allowed to warm to room temperature and stirred for 1 hr. The reaction was then diluted with dichloromethane (500 ml), washed with 1N aqueous hydrochloric acid (200 ml), dried over magnesium sulphate, and evaporated to afford benzyl 3-(hydroxymethyl)-1-piperidinecarboxylate as an oil (12.4 g).

Workup

  1. washwashed with 1N aqueous hydrochloric acid (200 ml)
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-7f0a59083c3b4b7b8eceb5ee96b4ae57
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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