Benzyl chloroformate → Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1634741Notes

Reaction equation

HRID 1634741 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:12][CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:8][C:9]([N:17]1[CH2:18][CH2:19][CH:14]([CH2:13][OH:12])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 4207714-Piperidinemethanol

Product 1

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 42.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of benzylchloroformate (17 g, 100 mmol) in 50 mL of 2-butanone was added dropwise to a stirred mixture of 4-hydroxymethylpiperidine (10.3 g, 100 mol) and potassium carbonate (13.8 g, 100 mmol) in 300 mL of 2-butanone. When the addition was complete the stirring was continued for an additional 3 hours. The solids formed were filtered and the filtrate concentrated in vacuo. Pure product was obtained by flash chromatography (hexane-ethyl acetate, 2:1) to give 10.6 g of product as an oil.

Workup

  1. additionWhen the addition
  2. customThe solids formed
  3. filtrationwere filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customPure product was obtained by flash chromatography (hexane-ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-c21d32acc7d044a1b9f78ac77f3c8abb
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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