Formic Acid → rac-methyl (1R,2R)-2-amino-1-hydroxycyclopentane-1-carboxylate
Reaction equation
C([N:8]([C@@H](C1C=CC=CC=1)C)[C@@H:9]1[CH2:13][CH2:12][CH2:11][C@:10]1([OH:18])[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@:10]1([OH:18])[C:14]([O:16][CH3:17])=[O:15]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a solution of methyl (1R,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-hydroxycyclopentanecarboxylate (0.75 g, 2.1 mmol) in methanol (30 mL) was added formic acid (1.44 mL) and 10% Pd/C (0.5 g). The mixture was purged with nitrogen followed by hydrogen and allowed to stir at 40° C. for 3 h under 1 atmosphere of hydrogen. The reaction mixture was then filtered through celite. Hydrochloric acid (1 mL, 12 M) was added to the filtrate, which was then concentrated and chased three times with methanol/benzene (1:1) to afford methyl (1R,2R)-2-amino-1-hydroxycyclopentanecarboxylate as a white solid (0.415 g, 100%). MS: 160.1 (M+H)+
Workup
- customThe mixture was purged with nitrogen
- filtrationThe reaction mixture was then filtered through celite
- additionHydrochloric acid (1 mL, 12 M) was added to the filtrate, which
- concentrationwas then concentrated
Sources & evidence
- ORD record
- ord-e7c1b6722ab64d769de95297a1047031
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595327B2
Reaction notes
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