Benzylamine → 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

HRID 1864807Notes

Reaction equation

HRID 1864807 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H:9]12[C:15](=O)[O:14][C:12](=[O:13])[C@@H:10]1[CH2:11]2>>[CH2:1]([N:8]1[C:12](=[O:13])[CH:10]2[CH:9]([CH2:11]2)[C:15]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 12688062(1r,5s)-3-Oxabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 27645863-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione

Conditions

Temperature
180 °C

Procedure

Benzylamine (8.8 mmol, 9.97 ml) was added dropwise to ice cooled cis-1,2-cyclopropanedicarboxylic acid anhydride (8.8 mmol, 0.99 g). After that the mixture was heated to 180° C. for 2 h on an oil bath. After cooling to r.t. the resulting solid oil was recrystallised from isopropanol.

Workup

  1. temperatureAfter cooling to r.t. the resulting solid oil
  2. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-e2274b205ecf4871a979796d24b0ee64
Source dataset
uspto-grants-2009_12
Patent number
US07625939B2

Reaction notes

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