3-Amino-1-propanol → 3-(3-Hydroxypropyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 132823Notes

Reaction equation

HRID 132823 reaction equation
[CH2:1]1[CH:3]2[C:4]([O:6][C:7](=[O:8])[CH:2]12)=O.[NH2:9][CH2:10][CH2:11][CH2:12][OH:13]>>[OH:13][CH2:12][CH2:11][CH2:10][N:9]1[C:7](=[O:8])[CH:2]2[CH:3]([CH2:1]2)[C:4]1=[O:6]

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Product 1

HCID 612069603-(3-Hydroxypropyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 49%

Conditions

Temperature
180 °C

Procedure

A mixture of cyclopropane-2,3-dicarboxylic acid anhydride (purchased at Acros, Ref 37012-0010, 500 mg, 1.0 eq.) and 3-amino-1-propanol (340 mL, 1.0 eq.) was heated 6 h at 180° C. The reaction mixture was purified on silica, eluting with a 98:2 to 19:1 gradient of dichloromethane/methanol, to yield 360 mg (49%) of the desired product as light yellow solid. MS (m/e): 168.1 (M−H−, 100%)

Workup

  1. customThe reaction mixture was purified on silica
  2. washeluting with a 98:2 to 19:1 gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-af3b9f43c5cb46fbb6b027663f7badf1
Source dataset
uspto-grants-2008_06
Patent number
US07388095B2

Reaction notes

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