Pyridine → 2-Aza-spiro[4.5]decane-2,4-dicarboxylic acid 2-benzyl ester 4-methyl ester
Reaction equation
Cl.[CH2:2]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:5]([C:12]([OH:14])=[O:13])[CH2:4][NH:3]1.N1C=CC=C[CH:16]=1.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH3:16][O:13][C:12]([CH:5]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:2][N:3]([C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[CH2:4]1)=[O:14]Participants
Procedure
A solution of (4) (3 g; 10.44 mmol) and 10% Pd (OH)2/C (0.60 g; 20% w/w) in methanol (50 mL) was stirred for 24 hours at 40° C. under at atmosphere of dry hydrogen gas. The catalyst was filtered off through a celite pad, and the filtrate was concentrated in vacuo to give 2 g (10.14 mmol; 97%) of (5) as a colorless oil which was used without any further purification. To a solution of (5) (2 g; 10.14 mmol) in dry dichloromethane (100 mL) was successively added, at 0° C., under an argon atmosphere, pyridine (2.04 mL; 25.35 mmol), and benzylchloroformate (2.89 mL; 20.24 mmol). The reaction mixture was then allowed to stir at room temperature for 2 days. The reaction mixture was washed (2×50 mL) with 1N HCl, dried over MgSO4, and concentrated in vacuo. The crude oil was purified by silica-gel flash chromatography in ether/heptane (1:1) to give 2.97 g (8.96 mmol; 88%) of (6) as a colorless oil.
Workup
- customwas used without any further purification
- washThe reaction mixture was washed (2×50 mL) with 1N HCl
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude oil was purified by silica-gel flash chromatography in ether/heptane (1:1)
Sources & evidence
- ORD record
- ord-b935bb18d68743bca9cd56ec7397e4d4
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316638B1
Reaction notes
Loading…