Lithium hydroxide, monohydrate → HCID 44125118, compound

HRID 601802Notes

Reaction equation

HRID 601802 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][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:4][CH:3]=1.O.[OH-].[Li+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][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:19][CH:20]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180242HCID 59180242, compound

Product 1

HCID 44125118HCID 44125118, compoundYield 74.3%

Procedure

The title compound was synthesized from methyl 4-(4-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (85 mg, 0.293 mmol) and lithium hydroxide monohydrate (67 mg, 1.58 mmol) according to General Procedure 7. The crude product was purified by flash chromatography (0-80% EtOAc/Heptane) to give 4-(4-chlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (14) as a light red solid (60 mg, 69%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.04-2.14 (m, 1H), 2.42-2.59 (m, 1H), 2.59-2.65 (m, 2H), 2.72 (dd, J=13.37, 7.91, 1H), 2.78 (dd, J=13.37, 6.83, 1H), 3.21-3.29 (m, 1H), 6.29 (s, 1H), 7.14-7.19 (m, 2H), 7.24-7.28 (m, 2H); LCMS-MS (ESI+) 274.2 (M−H); HPLC (UV=100%).

Workup

  1. customThe crude product was purified by flash chromatography (0-80% EtOAc/Heptane)

Sources & evidence

ORD record
ord-7372ec26edf64b4ca2e6378923f67cdd
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…