Methyl Isocyanate → HCID 9948235, compound

HRID 1613469Notes

Reaction equation

[CH:1]1([NH:4][CH:5]2[C:9]3[N:10]([CH3:18])[C:11]4[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][C:16]=4[C:8]=3[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.N12CCCN=C1CCCCC2.[CH3:30][N:31]=[C:32]=[O:33].CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH3:30][NH:31][C:32](=[O:33])[O:17][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([CH3:18])[C:9]3[CH:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)[CH2:6][CH2:7][C:8]=3[C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(N-Cyclopropyl)amino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol (2.2 g) was dissolved in CH2Cl2 (200 ml) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 0.21 g) and the solution was cooled to 0° C. A solution of methyl isocyanate (0.52 g in 30 ml CH2Cl2) was added slowly to the cooled solution and the reaction was monitored by thin layer chromatography (silica gel, 1:1 hexane/ethyl acetate). After warming to room temperature, the mixture was washed successively with water (2×100 ml), brine (1×100 ml) and again with water (1×100 ml). The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The crude material was recrystallized from acetonitrile. 3-(N-Cyclo-propyl)amino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]indol-7-yl methylcarbamate was isolated as light yellow/white plates (1.0 g).

Workup

temperatureAfter warming to room temperature
washthe mixture was washed successively with water (2×100 ml), brine (1×100 ml) and again with water (1×100 ml)
dry with materialThe organic layer was dried over Na2SO4
customthe solvent removed in vacuo
customThe crude material was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-87e6b9c37f044b9ca1bcd09718932f11
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05192789

Reaction notes

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