Sodium Hydroxide → 1-(1-(4-fluorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid

HRID 83595Notes

Reaction equation

[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=[O:21])[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]([OH:22])=[O:21])[CH2:18][CH2:19]2)=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 1-(1-(4-fluorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylate (197 mg, 0.550 mmol) was dissolved in EtOH (6 mL), and 7M aq. NaOH was added (6 mL). The reaction was allowed to stir at 60° C. for 8 h. EtOH was then removed in vacuo, and the remaining aqueous solution was acidified (to ˜pH 2) by conc. HCl. The precipitate was filtered over a scintered glass filter and collected as a viscous oil. This material was dried overnight under high-vacuum to afford 169 mg of the title compound.

Workup

customEtOH was then removed in vacuo
filtrationThe precipitate was filtered over a scintered glass
filtrationfilter
customcollected as a viscous oil
customThis material was dried overnight under high-vacuum

Sources & evidence

ORD record: ord-7d5b10ec40ae4c62acc4c179d0ce8e9d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846684B2

Reaction notes

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