Sodium Hydroxide → 6-Phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601902Notes

Reaction equation

[CH2:1]([CH:9]1[C:13]2[NH:14][C:15]([C:17]([O:19]CC)=[O:18])=[CH:16][C:12]=2[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>>[CH2:1]([CH:9]1[C:13]2[NH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:12]=2[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 59180187Ethyl 6-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 441252506-Phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 28.6%

Procedure

The title compound was synthesized from ethyl 6-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (87.3 mg, 0.31 mmol) and NaOH according to General Procedure 7. The crude product was purified by preparative HPLC (50%-100% methanol/water with 1% formic acid and 1% acetonitrile) to afford 22.6 mg of 6-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (27) in 29% yield. LCMS m/e 254 (M−H); 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.18-7.28 (m, 4H), 7.11-7.17 (m, 1H), 6.58 (s, 1H), 3.00-3.10 (m, 1H), 2.48-2.71 (m, 5H), 2.00-2.15 (m, 2H), 1.66-1.79 (m, 1H).

Workup

customThe crude product was purified by preparative HPLC (50%-100% methanol/water with 1% formic acid and 1% acetonitrile)

Sources & evidence

ORD record: ord-04e2e49648e84c4b85611e33ebd1cb58
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

Loading…