Methanol → Piperidine-1,2,6-tricarboxylic Acid 1-Benzyl Ester 2-Methyl Ester

HRID 987089Notes

Reaction equation

HRID 987089 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:21])[O:14][C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][OH:23]>>[CH3:22][O:23][C:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH:12]([C:13]([OH:14])=[O:21])[N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])=[O:20]

Participants

3

Reactant 2

HCID 887MethanolHCID 544831212,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester2×

Product 1

HCID 54189295Piperidine-1,2,6-tricarboxylic Acid 1-Benzyl Ester 2-Methyl EsterYield 96%

Procedure

2,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 2, 10 g, 34.51 mmol) was dissolved in methanol (50 ml). The reaction mixture was stirred at room temperature for 2 hours. The MeOH was evaporated to afford Compound 232 (10 g, 96%). Rf=0.47 (10% MeOH/CH2Cl2). The material was of sufficiently good quality to be used in the next reaction without purification.

Workup

  1. customThe MeOH was evaporated

Sources & evidence

ORD record
ord-2fe0f20c23734e24b4dd46b131d2fa93
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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