methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylate → methyl (1S,2R)-2-amino-1-methylcyclopentanecarboxylate

HRID 736818Notes

Reaction equation

HRID 736818 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([CH3:18])[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1>[Pd].C(O)=O.CO>[NH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@:10]1([CH3:18])[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 86607912methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylate

Product 1

HCID 86607913methyl (1S,2R)-2-amino-1-methylcyclopentanecarboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

According to the procedure of Example 53, Step 2, using methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylate (1.025 g, 2.92 mmol), 4.4% HCO2H/MeOH (30 mL) and 10% Pd/C (1.058 g), methyl (1S,2R)-2-amino -1-methylcyclopentanecarboxylate (527 mg, 2.72 mmol, 93%) was obtained as a colorless solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.29 (s, 3H) 1.56-1.62 (m, 1H) 1.64-1.76 (m, 3H) 2.07-2.13 (m, 1H) 2.15-2.22 (m, 1H) 3.24-3.31 (m, 1H) 3.64-3.71 (m, 3H) 8.18 (s, 3H).

Sources & evidence

ORD record
ord-fbc15acac26747b2a9494d0fb8823780
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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