Reaction #84688

ord-a5f92f3e41e34c1db6d01b91d4f96d55

Reaction equation

C[Si](C)(C)CCOC(=O)N[C@H]1C[C@@H]2C[C@@H]2[C@H]1N1C(=O)c2ccccc2C1=O
2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate
NN
hydrazine
→
C[Si](C)(C)CCOC(=O)N[C@H]1C[C@@H]2C[C@@H]2[C@H]1N
title compound
Yield 80.3%
C[Si](C)(C)CCOC(=O)N[C@H]1C[C@@H]2C[C@@H]2[C@H]1N
2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-aminobicyclo[3.1.0]hexan-3-ylcarbamate
Yield 80.3%

Reactants

C[Si](C)(C)CCOC(=O)N[C@H]1C[C@@H]2C[C@@H]2[C@H]1N1C(=O)c2ccccc2C1=O
2-(trimethylsilyl)ethyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate
NN
hydrazine

Reagents

None

Solvents

CCO
ethanol

Conditions

Temperature
75°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction solution was concentrated
  2. 2
    Otherthe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:4)

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434700B2uspto-grants-2016_09