4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid
Reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[CH2:10](C([O-])=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:20](=O)([O-:22])[O-:21].[Na+].[Na+]>>[C:20]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)([O:22][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:21]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Isonipecotic acid (5 g) was dissolved in 10% sodium carbonate (100 ml) and cooled to 0° C. Then benzylformate (6.6 ml) was added dropwise and stirred at 0° C. for 30 minutes. The reaction mixture was then removed to an ice bath and stirred for 18 hours. The reaction mixture was then poured into 2 M hydrochloric acid (100 ml). Ethyl acetate (300 ml) was added and the organic layer taken and washed with hydrochloric acid (2×100 ml) and saturated sodium chloride (75 ml). The organic layer was dried over magnesium sulphate, filtered and the solvent evaporated to form CBZ-isonipecotic acid.
Workup
- customThe reaction mixture was then removed to an ice bath
- stirringstirred for 18 hours
- additionThe reaction mixture was then poured into 2 M hydrochloric acid (100 ml)
- additionEthyl acetate (300 ml) was added
- washwashed with hydrochloric acid (2×100 ml) and saturated sodium chloride (75 ml)
- dry with materialThe organic layer was dried over magnesium sulphate
- filtrationfiltered
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-08e8eae285d446b2bc2eb3aad57d014b
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06489481B1
Reaction notes
Loading…