Reaction #2122509

ord-3c42570751e74046a7d9746012cf09ba

Reaction equation

CC1(C)[C@@H]2[C@@H](C#N)NC[C@@H]21
(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carbonitrile
COC(=O)[C@H]1NC[C@H]2[C@@H]1C2(C)C
(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester
→
COC(=O)C1NCC2C1C2(C)C
6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester

Reactants

CC1(C)[C@@H]2[C@@H](C#N)NC[C@@H]21
(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carbonitrile
COC(=O)[C@H]1NC[C@H]2[C@@H]1C2(C)C
(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carbonitrile prepared according to Example 16 or 17 is converted to the corresponding substantially enantiomerically pure (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester by the procedure described in PCT International Application Publication WO 2007/075790.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08574876B2uspto-grants-2013_11