Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate → Ethyl 2-(3-phenylcyclobutyl)propanoate

HRID 1713907Notes

Reaction equation

HRID 1713907 reaction equation
NC1C=CC(CC2CC(C(OCC)=O)C2)=CC=1.[C:18]1([CH:24]2[CH2:27][C:26](=[C:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([CH:24]2[CH2:25][CH:26]([CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 59464168Ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate2×HCID 59464266Ethyl 2-(3-phenylcyclobutylidene)propanoate

Product 1

HCID 59464131Ethyl 2-(3-phenylcyclobutyl)propanoate

Procedure

Following the general procedure described for ethyl 3-(4-aminobenzyl)cyclobutanecarboxylate (Intermediate 931i), replacing ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate with ethyl 2-(3-phenylcyclobutylidene)propanoate the title compound was obtained without chromatography; 1H NMR δ (CDCl3): 1.08-1.10 (0.75H, d), 1.12-1.15 (3.25H, d), 1.22-1.30 (3H, m), 2.17-2.64 (6H, m), 3.34 (0.25H, m), 3.48-3.54 (0.75H, m), 4.09-4.18 (2H, m), 7.15-7.36 (5H, m); MS m/e MH+ 233.

Sources & evidence

ORD record
ord-87382fa441af4ab29aed6eab020e1f8f
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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