Formic Acid → methyl (1S,2R)-2-amino-1-ethylcyclopentanecarboxylate

HRID 736824Notes

Reaction equation

HRID 736824 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([CH2:18][CH3:19])[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([CH2:18][CH3:19])[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86607916HCID 86607916, compound

Product 1

HCID 86607915methyl (1S,2R)-2-amino-1-ethylcyclopentanecarboxylateYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

According to the procedure of Example 53, Step 2, using crude methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-ethylcyclopentanecarboxylate (1.103 g), 4.4% formic acid in methanol (30 mL) and 10% Pd/C (2 g), methyl (1S,2R)-2-amino-1-ethylcyclopentanecarboxylate (441 mg, 2.12 mmol, 21%) was obtained as a colorless solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.78 (t, J=7.45 Hz, 3H) 1.42 (ddd, J=21.10, 7.58, 7.45 Hz, 1H) 1.50-1.78 (m, 5H) 1.92 (ddd, J=21.03, 7.42 Hz, 1H) 2.01-2.12 (m, 1H) 2.16-2.26 (m, 1H) 3.31 (s, 1H) 3.68 (s, 3H) 8.15 (s, 2H).

Sources & evidence

ORD record
ord-989cca04950b485daef267d2dc2ef428
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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