Water → HCID 22861115, compound
Reaction equation
[C:1]([NH:8][CH2:9][C@H:10]1[CH2:12][C@H:11]1[CH2:13][O:14][N:15]1C(=O)C2C(=CC=CC=2)C1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O>C(Cl)Cl>[O:14]([CH2:13][C@H:11]1[CH2:12][C@H:10]1[CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[NH2:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1.5 g (0.00433 mol) of 2-[cis-2-(N-BOC-aminomethyl)-cyclopropylmethoxy]-1H-isoindole-1,3(2H)-dione and 9 ml of hydrazinc hydrate is stirred at room temperature for 1/2 hour. 9 ml of water are then added to the reaction mixture and, after a further 1/2 hour, 50 ml of methylene chloride are added. The reaction mixture is further stirred for another 3 hours, the methylene chloride phase is then separated off and the aqueous phase is washed twice with 30 ml of methylene chloride each time. The combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The oily cis-2-aminoxymethyl-N-BOC-cyclopropylmethylamine thus obtained, Rf value=0.13 (silica gel/ethyl acetate:hexane (1:1)), is dissolved in 18 ml of 3M methanolic hydrochloric acid and the reaction mixture is stirred at room temperature for 1 hour. After addition of diethyl ether and cooling in an ice-bath, the title compound which has crystallized out is filtered off, washed with diethyl ether and dried, m.p. 178°-180° C. (decomp.).