Ammonia → HCID 9794602, compound

HRID 849671Notes

Reaction equation

[C:1]([C@@H:3]([NH:12][C@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])[C:4]1([C:7](OCC)=[O:8])[CH2:6][CH2:5]1)#[N:2].N.[H][H]>[Ni]>[C:15]1([C@@H:13]([NH:12][C@H:3]2[C:4]3([CH2:6][CH2:5]3)[C:7](=[O:8])[NH:2][CH2:1]2)[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 180 °C

Procedure

An autoclave was charged with 1.0 g of 1-[(S)-1-cyano-[(S)-1-phenylethylamino]methyl]-1-ethoxycarbonylcyclopropane, 1.7 ml of Raney nickel and 17 ml of ammonia-saturated ethanol, and the contents were stirred at room temperature for 1.5 hours in an atmosphere of hydrogen under a pressure of 35 kg/cm2. After completion of the reaction, the catalyst was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in 20 ml of ethanol, put into an autoclave and heated at 180° C. for 8.5 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure, and the resulting residue was mixed with isopropanol and stirred to obtain 621 mg (74%) of the title compound in the form of slightly yellow crystals. The thus obtained compound was recrystallized from ethanol and isopropanol, and used as a sample for analyses.

Workup

customAfter completion of the reaction
customthe catalyst was removed by filtration
concentrationthe resulting filtrate was concentrated under a reduced pressure
dissolutionThe resulting residue was dissolved in 20 ml of ethanol
customAfter completion of the reaction
customthe solvent was evaporated under a reduced pressure
additionthe resulting residue was mixed with isopropanol

Sources & evidence

ORD record: ord-03f6fb5798c24dd6a95f71a9575a3d1b
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013806

Reaction notes

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