HCID 53735847, compound → HCID 54416234, compound
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]([OH:15])CO)[N:6]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:4]>CCOCC.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]=[O:15])[N:6]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
6-(2,3-Dihydroxy-propyl)-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (Compound 235, 0.614 g, 1.75 mmol) was dissolved in Et2O (20 mL) and cooled to 0° C. Ten percent NaIO4 aqueous solution (4 mL) was added, and the reaction was stirred for 1 hour. The reaction mixture was poured into brine (15 mL) and extracted with Et2O (3×20 mL). The combined organic layer was further washed with aqueous NaS2O3 (10 mL), NaHCO3 saturated solution (10 mL), brine (10 mL) and finally dried over MgSO4. The solvents were removed to afford Compound 236 (0.53 g, 95%). Rf=0.67 (1:1 EtOAc/hexanes). The material was of sufficiently good quality to be used in the next reaction without purification.
Workup
- extractionextracted with Et2O (3×20 mL)
- washThe combined organic layer was further washed with aqueous NaS2O3 (10 mL), NaHCO3 saturated solution (10 mL), brine (10 mL)
- dry with materialfinally dried over MgSO4
- customThe solvents were removed
Sources & evidence
- ORD record
- ord-9e069212723545a08b31f9f7b84ec4f9
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06630472B1
Reaction notes
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