Ammonia → HCID 55281684, compound

HRID 1807665Notes

Reaction equation

HRID 1807665 reaction equation
C([O:3][C:4]([C@:6]12[CH2:11][C@H:10]1[CH2:9][CH2:8][NH:7]2)=O)C.[NH3:12]>CO>[C@:6]12([C:4]([NH2:12])=[O:3])[CH2:11][C@H:10]1[CH2:9][CH2:8][NH:7]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66890285HCID 66890285, compound

Product 1

HCID 55281684HCID 55281684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1S,5R)-2-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (2.5 g, prepared by the procedure of Hercouet Tetrahedron Asymmetry 1996, 7, 1267-1268.) and 7 M ammonia in MeOH (20 ml) was heated in a sealed vessel at 80° C. for 5 days. The cooled RM was evaporated and triturated with hexanes/DCM to give the title compound as a beige solid. 1H-NMR (DMSO-d6, 400 MHz): 7.15 (s, 1H), 7.04 (s, 1H), 3.00-2.91 (m, 1H), 2.67 (q, 1H), 1.94-1.83 (m, 1H), 1.74-1.67 (m, 1H), 1.64-1.55 (m, 1H), 1.38-1.31 (m, 1H), 0.90 (t, 1H)).

Workup

  1. customprepared by the procedure of Hercouet Tetrahedron Asymmetry 1996, 7, 1267-1268
  2. customThe cooled RM was evaporated
  3. customtriturated with hexanes/DCM

Sources & evidence

ORD record
ord-d6a21081dbd64eefa9410789e27ef913
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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