Water → HCID 22861115, compound

HRID 439892Notes

Reaction equation

HRID 439892 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

HCID 962WaterHCID 22861110HCID 22861110, compound

Product 1

HCID 22861115HCID 22861115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.).

Workup

  1. stirringThe reaction mixture is further stirred for another 3 hours
  2. customthe methylene chloride phase is then separated off
  3. washthe aqueous phase is washed twice with 30 ml of methylene chloride each time
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e2946d402f0f4619b6396b7f7d7f9a4e
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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