2,6-Dimethyl-1-piperidineethanamine → (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide
Reaction equation
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([OH:13])=O)[C:6]1=[O:14])(=[O:3])[CH3:2].[CH3:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH2:25]>O1CCCC1>[CH3:15][C@H:16]1[CH2:21][CH2:20][CH2:19][C@@H:18]([CH3:22])[N:17]1[CH2:23][CH2:24][NH:25][C:11](=[O:13])[CH2:10][N:7]1[CH2:8][CH2:9][CH:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]1=[O:14]Participants
4
Procedure
1.0 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid is placed in 15 ml of absolute tetrahydrofuran, whereupon 0.89 g of N,N'-carbonyldiimidazole is added in one portion. The mixture is stirred at room temperature until the gas evolution is complete. Thereafter, 0.86 g of 94.7% cis-(2-(2,6-dimethyl-1-piperidinyl)ethylamine is added and the mixture is left to stand overnight at room temperature and then evaporated. The residue is chromatographed on 60 g of aluminum oxide (activity grade III, neutral). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride has a melting point of 121°-122° after trituration with diethyl ether.
Workup
- additionis added in one portion
- waitthe mixture is left
- customevaporated
- customThe residue is chromatographed on 60 g of aluminum oxide (activity grade III, neutral)
- washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride
Sources & evidence
- ORD record
- ord-312945ea9d1449e1b7e9e3b7000f2a13
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04476308
Reaction notes
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