Water → rac-tert-butyl N-((1R,2S)-2-aminocyclopentyl)carbamate

HRID 546410Notes

Reaction equation

HRID 546410 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>ClCCl.C(N(CC)CC)C>[C:8]([O:12][C:13]([NH:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:1]1[NH2:7])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2×HCID 11412654cis-Cyclopentane-1,2-diamine

Product 1

HCID 18442856rac-tert-butyl N-((1R,2S)-2-aminocyclopentyl)carbamateYield 98.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

cis-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in dichloromethane (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 saline and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=9:1) to obtain the title compound (395 mg) as a pale yellow oil.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 7 hours
  3. customto separate an organic layer
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by flash column chromatography on silica gel (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-f1b68db288d346b3aaf75f72f2383ae3
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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