Ammonium Hydroxide → (3R,4R)-benzyl 4-amino-3-hydroxy-3-methylpyrrolidine-1-carboxylate
反応式
[CH3:1][C@:2]12[O:7][C@H:6]1[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3]2.[OH-].[NH4+:19]>O1CCOCC1>[NH2:19][C@@H:6]1[CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][C@:2]1([OH:7])[CH3:1]参加物
4
反応条件
- 温度
- 100 °C
実験手順
A mixture of (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (4.50 g, 19.29 mmol) and concentrated ammonium hydroxide (16 mL, 411 mmol) in dioxane (8 mL) in a sealed vessel was heated to 100° C. for 15 h. The resulting mixture was concentrated to afford (3R,4R)-benzyl 4-amino-3-hydroxy-3-methylpyrrolidine-1-carboxylate along with its regioisomer (4.8 g, 85:15 ratio), which was used in the next step without purification. MS (ES+) m/z: 218.2 (M+H).