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

HRID 2268943Notes

Reaction equation

HRID 2268943 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C([O-])(O)=O.[Na+].[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[CH2:14]([O:21][C:22]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 107308Piperidin-3-ylmethanolHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-hydroxymethylpiperidine (5 g, 43.4 mmol, 1 eq) in CHCl3 (150 mL) was added saturated aqueous NaHCO3 (150 mL). To the vigorously stirred mixture was added benzyl-chloroformate (6.8 mnL, 47.74 mmol, 1.1 eq) via syringe. The mixture was stirred 5 h. The layers were separated and the aqueous layer was extracted 2× with CH2Cl2. The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated. The material was used crude.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted 2× with CH2Cl2
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd1fa89b454a4170896e96435f968e4f
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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