Ethanol → rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

HRID 871868Notes

Reaction equation

HRID 871868 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:6][CH:5]=1)([O-])=O.C(O)C>C(OCC)(=O)C.[Pt](=O)=O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 86673141HCID 86673141, compound

Product 1

HCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamateYield 85%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.39 g (5.0 mmol) of the product prepared in step 15.2 are dissolved in 25 mL of hot ethyl acetate. After cooling to room temperature, 25 mL of absolute ethanol and 0.057 g (0.25 mmol) of platinum (IV) oxide are successively added. The reaction mixture is placed under a hydrogen pressure of 2.75 bar for 2 hours, and is filtered through thin glass fibre paper. The filtrate is concentrated under vacuum and purified by chromatography on a column of silica, eluting with a cyclohexane/ethyl acetate gradient (from 70/30 to 55/45). 1.05 g of the expected product are obtained. Yield=85%.

Workup

  1. customfor 2 hours
  2. filtrationis filtered through thin glass fibre paper
  3. concentrationThe filtrate is concentrated under vacuum
  4. custompurified by chromatography on a column of silica
  5. washeluting with a cyclohexane/ethyl acetate gradient (from 70/30 to 55/45)

Sources & evidence

ORD record
ord-c3bb768bf6c647ffba216bded22ee1d0
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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