Tetrahydrofuran → HCID 22611929, compound

HRID 843713Notes

Reaction equation

HRID 843713 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29]CC)=[O:28])[CH2:22]2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.OS([O-])(=O)=O.[K+]>O.C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([OH:29])=[O:28])[CH2:22]2)=[O:20])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 22611770HCID 22611770, compound

Product 1

HCID 22611929HCID 22611929, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 1-[2-(1-benzyloxycarbonyl-4-piperidyloxy)acetyl]-3-piperidinecarboxylate (2.06 g) and 1N NaOH aqueous solution (14.29 ml) in a solution of tetrahydrofuran (10 ml), ethanol (10 ml) and water (10 ml) was stirred for 1 hour at ambient temperature. The mixture was acidified with 10% aqueous solution of KHSO4 and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 1-[2-(1-benzyloxycarbonyl-4-piperidyloxy)acetyl]-3-piperidinecarboxylic acid (1.51 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-d9a56903b1824c289c68193485d3e6fc
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

Loading…