Hydrazine → 2-trimethylsilylethyl N-[(1S,2R,3S,5S)-2-amino-3-bicyclo[3.1.0]hexanyl]carbamate
Reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@H:12]1[C@@H:17]([NH:18][C:19](=[O:27])[O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][C@H:15]2[C@@H:13]1[CH2:14]2.NN>C(O)C>[NH2:3][C@H:12]1[C@@H:17]([NH:18][C:19](=[O:27])[O:20][CH2:21][CH2:22][Si:23]([CH3:25])([CH3:24])[CH3:26])[CH2:16][C@H:15]2[C@@H:13]1[CH2:14]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of 2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate (1.5 g, 3.886 mmol) in ethanol (20 mL) at room temperature was added hydrazine (1.9 ml, 38.860 mmol), and the resulting mixture was stirred at 75° C. for 2 hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4) to afford the title compound (800 mg, 80%) as a light yellow semi-solid.
Workup
- concentrationThe reaction solution was concentrated
- customthe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4)
Sources & evidence
- ORD record
- ord-a5f92f3e41e34c1db6d01b91d4f96d55
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434700B2
Reaction notes
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