{1-[1-(4-Pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester → 1-Amino-cyclopropanecarboxylic acid [1-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropyl]-amide
Reaction equation
C(OC(=O)[NH:10][C:11]1([C:14](=[O:31])[NH:15][C:16]2([C:19]3[CH:24]=[C:23]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH:22]=[CH:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[N:26]1([CH2:25][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([C:16]3([NH:15][C:14]([C:11]4([NH2:10])[CH2:12][CH2:13]4)=[O:31])[CH2:17][CH2:18]3)[CH:24]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 100 mL one neck round bottom flask, {1-[1-(4-Pyrrolidin-1-ylmethyl-pyridin-2-yl)-cyclopropylcarbamoyl]-cyclopropyl}-carbamic acid benzyl ester (67 mg, 0.154 mmol) was dissolved in MeOH (10 mL). 10 Wt. % Pd/C (15 mg) was then added. Nitrogen gas was bubbled through the suspension for 10 min. The reaction flask was evacuated and then filled with H2. This purging process was repeated twice and then the reaction was allowed to stir for 16 h under H2 (1 atm). The reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to afford 39.3 mg of the title compound as a white solid.
Workup
- customNitrogen gas was bubbled through the suspension for 10 min
- customThe reaction flask was evacuated
- additionfilled with H2
- filtrationThe reaction mixture was filtered through celite
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-35bd872fe9dc496ea7199136ceaf7d91
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552205B2
Reaction notes
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