Ethyl 3-(5-cyclopentyl-4-methoxycarbonyloxy-2-nitro-phenyl)propanoate → Ethyl 3-(2-amino-5-cyclopentyl-4-(methoxycarbonyloxy)phenyl)propanoate

HRID 383383Notes

Reaction equation

HRID 383383 reaction equation
[CH:1]1([C:6]2[C:7]([O:22][C:23]([O:25][CH3:26])=[O:24])=[CH:8][C:9]([N+:19]([O-])=O)=[C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd]>[NH2:19][C:9]1[CH:8]=[C:7]([O:22][C:23]([O:25][CH3:26])=[O:24])[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:11][C:10]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 1

HCID 59395000Ethyl 3-(5-cyclopentyl-4-methoxycarbonyloxy-2-nitro-phenyl)propanoate

Product 1

HCID 59395047Ethyl 3-(2-amino-5-cyclopentyl-4-(methoxycarbonyloxy)phenyl)propanoateYield 74%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask containing ethyl 3-(5-cyclopentyl-4-methoxycarbonyloxy-2-nitro-phenyl)propanoate (258 mg, 0.71 mmol) and 10% Pd/C (26 mg) was evacuated and flushed with N2. Ethanol (3 mL) was added and the reaction stirred for 6 h under H2 atmosphere. The reaction was filtered and the solvent was removed under reduced pressure to provide ethyl 3-(2-amino-5-cyclopentyl-4-(methoxycarbonyloxy)phenyl)propanoate (175 mg, 74% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.83 (s, 1H), 6.33 (s, 1H), 4.94 (s, 2H), 4.06-4.01 (m, 2H), 3.79 (s, 3H), 2.88-2.79 (m, 1H), 2.68 (t, J=7.4 Hz, 2H), 2.55-2.50 (m, obscured by DMSO peak, 2H), 1.84-1.77 (m, 2H), 1.72-1.66 (m, 2H), 1.62-1.55 (m, 2H), 1.45-1.36 (m, 2H), 1.17 (td, J=7.1, 3.4 Hz, 3H).

Workup

  1. customwas evacuated
  2. customflushed with N2
  3. additionEthanol (3 mL) was added
  4. filtrationThe reaction was filtered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3f3d60bb18d84136b4334c4da38087c0
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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