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

HRID 1711414Notes

Reaction equation

HRID 1711414 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:13]([O:12][C:10]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1)=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 4207714-PiperidinemethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidin-4-yl-methanol (0.57 g, 5 mmoles), benzyl chloroformate (0.75 ml, 5.5 mmoles), and sodium bicarbonate (0.46 g, 5.5 mmoles) in CH2Cl2 was stirred at room temperature for 2 hours, diluted with H2O and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound (0.95 g, 3.8 mmoles).

Workup

  1. extractionextracted with EtOAc
  2. washwashed sequentially with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08f50b5298184d6ba84068687409fed3
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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