Sodium Carbonate → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 602122Notes

Reaction equation

HRID 602122 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8]1.[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:15]([O:22][C:23]([N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution (20 mL) of sodium carbonate (6.90 g, 65.1 mmol) was added to 3-piperidinylmethanol (5.00 g, 43.4 mmol) in tetrahydrofuran (20 mL). While the mixture was chilled in an ice bath, benzyloxycarbonyl chloride (9.36 g, 52.1 mmol) was added and the mixture was stirred for 1 hour and subsequently 7 hours at room temperature. The solvent was then evaporated and ethyl acetate was added to the residue. The mixture was then washed sequentially with water, 0.1 mol/L hydrochloric acid and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1) gave 9.15 g (85%) of the desired compound as a colorless powder.

Workup

  1. temperatureWhile the mixture was chilled in an ice bath
  2. customThe solvent was then evaporated
  3. additionethyl acetate was added to the residue
  4. washThe mixture was then washed sequentially with water, 0.1 mol/L hydrochloric acid and brine
  5. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1)

Sources & evidence

ORD record
ord-2f1b4fe843c24303a816c714fdae7cb9
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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