Lithium hydroxide, monohydrate → 4-(Cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 601801Notes

Reaction equation

HRID 601801 reaction equation
[CH:1]1([CH2:7][CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([O:18]C)=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>>[CH:1]1([CH2:7][CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([OH:18])=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:1]1([CH2:7][CH:8]2[C:15]3[CH:14]=[C:13]([C:16]([O-:18])=[O:17])[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180172Methyl 4-(cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 2

HCID 441251164-(Cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acidHCID 866295514-(Cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylateYield 21%

Procedure

The title compound was synthesized from methyl 4-(cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate and lithium hydroxide monohydrate according to General Procedure 7. The crude product was dried onto silica gel and purified by chromatography (0 to 100% EtOAc/heptane) to give 4-(cyclohexylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate as a brown solid (0.018 g, 21%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.87-1.02 (m, 2H) 1.14-1.36 (m, 5H) 1.36-1.54 (m, 2H) 1.63-1.80 (m, 3H) 1.83-2.00 (m, 2H) 2.50-2.77 (m, 3H) 2.97-3.09 (m, 1H) 6.59 (s, 1H). LCMS m/e 248 (M+H). 97.5% pure by HPLC.

Workup

  1. dry with materialThe crude product was dried onto silica gel
  2. custompurified by chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-27b2bf819fba4ad79966bb23ac1e8a56
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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