Sodium Hydroxide → HCID 59180157, compound

HRID 601809Notes

Reaction equation

[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[OH-].[Na+]>>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([CH:7]2[C:14]3[CH:13]=[C:12]([C:15]([OH:17])=[O:16])[NH:11][C:10]=3[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 59180069HCID 59180069, compound

Product 1

HCID 59180157HCID 59180157, compoundYield 28%

Procedure

The title compound was synthesized from methyl 4-p-tolyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.2888 g, 1.2 mmol, 1 equiv) and sodium hydroxide (2.94 mL, 10 M, 25 equiv) according to General Procedure 7. The resulting product was purified by preparative HPLC (water with 0.1% formic acid and 1% acetonitrile/methanol; 50 mm Dynamax HPLC C-18 column; 28 mL/min; 60% to 100% methanol) to give 4-p-tolyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (37) (76.9 mg, 28%) 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.02-7.10 (m, 4H), 6.50 (s, 1H), 4.13 (t, J=7.20 Hz, 1H), 2.68-2.94 (m, 3H), 2.29 (s, 3H), 2.14-2.25 (m, 1H); LCMS m/e 240 (M−H).

Workup

customThe resulting product was purified by preparative HPLC (water with 0.1% formic acid and 1% acetonitrile/methanol; 50 mm Dynamax HPLC C-18 column; 28 mL/min; 60% to 100% methanol)

Sources & evidence

ORD record: ord-010467a819854cfd90548c405aad2cf4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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