Ethanol → Methyl 3-(3-aminopropoxy)benzoate

HRID 1713856Notes

Reaction equation

HRID 1713856 reaction equation
NC1C=CC(C2CCC(C(OC)=O)C2)=CC=1.C(OC([NH:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([O:37][CH3:38])=[O:36])=O)C1C=CC=CC=1.CCO>CCOC(C)=O>[NH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([O:37][CH3:38])=[O:36]

Participants

5

Reactant 3

HCID 702EthanolHCID 59464327Methyl 3-(4-aminophenyl)cyclopentanecarboxylate2×HCID 59464335Methyl 3-(3-{[(benzyloxy)carbonyl]amino}propoxy)benzoate

Product 1

HCID 59464150Methyl 3-(3-aminopropoxy)benzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described for methyl 3-(4-aminophenyl)cyclopentanecarboxylate, replacing methyl 3-(4-nitrophenyl)cyclopentanecarboxylate (Intermediate 84 (i)) with methyl 3-(3-{[(benzyloxy)carbonyl]amino}propoxy)benzoate and using EtOAc as solvent instead of EtOH the title compound was obtained; 1H NMR δ 1.77-1.83 (2H, m), 2.70 (2H, t), 3.86 (3H, s), 4.09 (2H, t), 7.21-7.23 (1H, m), 7.43 (2H, t), 7.54 (1H, d); MS m/e MH+ 210.

Sources & evidence

ORD record
ord-0959dae45e8f461fbabf79a0475327e7
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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