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(N(CC)CC)C.[C:15]([O:19][C:20](ON=C(C1C=CC=CC=1)C#N)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>C(Cl)Cl>[C:15]([O:19][C:20](=[O:21])[NH:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[NH2:7])([CH3:18])([CH3:17])[CH3:16]Participants
Conditions
- Temperature
- 0 °C
Procedure
(±)-trans-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in methylene chloride (10 mL), and to the solution were added triethylamine (1.1 mL) and 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) at 0° C., followed by stirring at 0° C. for 1 hour. Subsequently, additional 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) was added thereto, and the thus-obtained mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture to partition the mixture. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The residue was purified by silica gel flash column chromatography (methylene chloride:methanol=9:1), to thereby give the title compound (395 mg).
Workup
- stirringthe thus-obtained mixture was stirred at room temperature for 7 hours
- customto partition the mixture
- washThe organic layer was washed with saturated brine
- dry with materialwas dried over sodium sulfate anhydrate
- customThe residue was purified by silica gel flash column chromatography (methylene chloride:methanol=9:1)
Sources & evidence
- ORD record
- ord-bebed518f25a460696381fb45085a585
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576135B2
Reaction notes
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