Benzyl chloroformate → 2-{1-[(Benzyloxy)carbonyl]piperidin-3-yl}-2-hydroxyacetic acid

HRID 2050189Notes

Reaction equation

HRID 2050189 reaction equation
Cl.[OH:2][CH:3]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[OH:2][CH:3]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:23]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:24])[CH2:8]1)[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 70587825HCID 70587825, compound

Product 1

HCID 203422582-{1-[(Benzyloxy)carbonyl]piperidin-3-yl}-2-hydroxyacetic acidYield 90.4%

Procedure

To a solution of 2-hydroxy-2-(piperidin-3-yl)acetic acid hydrochloride (1.956 g; 10 mmoles) in 2.7 (w/w) % aqueous sodium hydroxide solution is added 1.72 ml (1.2 equivalents) of benzyloxycarbonylchloride. After 2 hours, the reaction mixture is washed twice with ether, adjusted to pH 1 to 2 with 10% hydrochloric acid, and extracted thrice with methylene chloride. The extract is washed with water, dried over sodium sulfate, and evaporated under reduced pressure to yield 2.650 g of oily 2-hydroxy-2-(1-benzyloxycarbonylpiperidin-3-yl) acetic acid in 90.4% yield.

Workup

  1. washthe reaction mixture is washed twice with ether
  2. extractionextracted thrice with methylene chloride
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c2dc6716c1384b349c3d2038c7f1be40
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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