Water → Methyl 2-(4-hydroxypiperidin-1-yl)acetate

HRID 1670826Notes

Reaction equation

HRID 1670826 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.N(CC)(CC)CC.Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].O>C(Cl)Cl>[CH3:20][O:19][C:17](=[O:18])[CH2:16][N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 79341Piperidin-4-ol

Product 1

HCID 28837753Methyl 2-(4-hydroxypiperidin-1-yl)acetateYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a 0° C. solution of 4-hydroxy-piperidine (20.0 g, 0.19 mol) and (CH3CH2)3N (24.0 g, 0.24 mol) in CH2Cl2 (200 mL) with methyl bromoacetate (30.21 g, 0.197 mol), warm to room temperature, and stir 2 hours at room temperature under N2. Dilute the reaction with water and extract with 3:1 chloroform:isopropanol. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 5% methanol in CH2Cl2 to afford 20.13 g (59%) of the titled product. Rf=0.13 (9/1 CH2Cl2/methanol). ES MS (m/z): 174 (M+).

Workup

  1. additionDilute
  2. extractionextract with 3:1 chloroform
  3. dry with materialDry the organic layer (Na2SO4)
  4. customremove the solvent in vacuo
  5. customto afford crude product
  6. custompurify with a 5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-6feb880458f54c73aec6f5c111342c02
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

Loading…