Hydrochloric Acid → 3-Cyclobutyl-3-aza bicyclo[3.1.0]hexane-6-carboxylic acid
Reaction equation
[CH:1]1([N:5]2[CH2:10][CH:9]3[CH:7]([CH:8]3[C:11]([O:13]CC)=[O:12])[CH2:6]2)[CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.[OH-].[Li+].Cl>O>[CH:1]1([N:5]2[CH2:10][CH:9]3[CH:7]([CH:8]3[C:11]([OH:13])=[O:12])[CH2:6]2)[CH2:2][CH2:3][CH2:4]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of ethyl 3-cyclobutyl-3-aza bicyclo[3.1.0]hexane-6-carboxylate (218 mg, 1.04 mmol, obtained in the above step), tetrahydrofuran (2 mL) and water (2.0 mL) cooled at 0° C., lithium hydroxide monohydrate (133 mg, 3.19 mmol) was added in a single lot. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was cooled again to 0° C. and acidified with 2N hydrochloric acid to pH: 2-3. The volatiles were removed under reduced pressure and the traces of water were removed by azeotropic distillation with toluene to obtain 3-cyclobutyl-3-aza bicyclo[3.1.0]hexane-6-carboxylic acid (180 mg).
Workup
- temperatureThe reaction mixture was cooled again to 0° C.
- customThe volatiles were removed under reduced pressure
- customthe traces of water were removed by azeotropic distillation with toluene
Sources & evidence
- ORD record
- ord-5fc38e6f302640fea2c554a615f20a45
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079894B2
Reaction notes
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