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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1092484Generated: October 25, 2026

2-(4-Hydroxyphenyl)-3-methylbutyric acid → N-[(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-(4-hydroxyphenyl)-3-methylbutanamide

https://huagongshe.com/reaction/1092484

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-(4-Hydroxyphenyl)-3-methylbutyric acidHCID 112192—
Reactant(S)-2-Phenylbutyric acidHCID 785329—
Reactant(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amineHCID 25918977—
ProductN-[(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-(4-hydroxyphenyl)-3-methylbutanamideHCID 66590581—

Reaction Steps

The title compound was prepared by substituting (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 33 for (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine and 2-(4-hydroxyphenyl)-3-methylbutanoic acid for (S)-2-phenylbutanoic acid in Step F of the procedure used to prepare Example 16: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.53-8.46 (m, 1H), 7.56 (d, J=2.8, 1H), 7.43 (d, J=7.2, 1H), 7.36 (dt, J=7.5, 18.2, 4H), 7.26 (q, J=7.1, 1H), 7.16 (dd, J=3.0, 8.6, 2H), 4.44-4.32 (m, 1H), 3.60 (d, J=13.1, 0.5H), 3.53 (d, J=13.1, 0.5H), 3.44 (d, J=13.2, 0.5H), 3.33 (d, J=13.1, 0.5H), 3.18 (d, J=10.4, 1H), 2.90 (dd, J=3.0, 9.1, 0.5H), 2.66 (s, 1H), 2.58 (d, J=8.8, 1H), 2.49 (t, J=10.5, 1H), 2.44-2.35 (m, J=10.0, 1H), 2.33-2.11 (m, 2H), 1.99-1.89 (m, 0.5H), 1.88-1.63 (m, 1.5H), 1.53-1.42 (m, 0.5H), 1.41-1.24 (m, 2H), 1.22 (dd, J=4.4, 6.3, 3H), 0.97-0.82 (m, J=21.9, 35.1, 1H), 0.79 (d, J=6.7, 3H); MS (ESI+) m/z 393 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08129417B2
Source datasetuspto-grants-2012_03
ORD IDord-4e62c7beddfd4fc7819ed651bccfd89c
Source noteuspto-grants-2012_03