Water → rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamate
Reaction equation
[C@@H:1]1([NH2:7])[CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:6].[C:8]([O:12][C:13](ON=C(C1C=CC=CC=1)C#N)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>C(Cl)Cl.C(N(CC)CC)C>[NH2:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[NH:7][C:13](=[O:14])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
(±)-trans-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in methylene chloride (10 ml), to which triethylamine (1.1 ml) and 2-(tert-butoxycarbonyloxy-imino)-2-phenylacetonitrile (493 mg) were added, and the mixture was stirred at 0° C. for 1 hour. Thereafter, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) were additionally added, and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture to separate an organic layer. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1) to obtain the title compound (395 mg).
Workup
- additionwere added
- stirringthe mixture was stirred at room temperature for 7 hours
- customto separate an organic layer
- washThe organic layer was washed with saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customThe residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1)
Sources & evidence
- ORD record
- ord-d7b5c3f55cfc4acd874224a669e9dfb8
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07342014B2
Reaction notes
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