Lithium hydroxide, monohydrate → HCID 59180084, compound

HRID 601804Notes

Reaction equation

HRID 601804 reaction equation
[CH2:1]([CH:9]1[C:16]2[CH:15]=[C:14]([C:17]([O:19]C)=[O:18])[NH:13][C:12]=2[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.[OH-].[Li+]>>[CH2:1]([CH:9]1[C:16]2[CH:15]=[C:14]([C:17]([OH:19])=[O:18])[NH:13][C:12]=2[CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59180061HCID 59180061, compound

Product 1

HCID 59180084HCID 59180084, compoundYield 84%

Procedure

The title compound was synthesized from methyl 4-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate and lithium hydroxide monohydrate (81 mg, 1.93 mmol) according to General Procedure 7. Silica gel was added, the solvent stripped off and the silica gel-imbedded material was purified by flash chromatography (0-80% EtOAc/Heptane) to give 4-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid (18) as a light yellow solid (103.6 mg, 84%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.68-1.87 (m, 2H), 1.98-2.09 (m, 1H), 2.55-2.80 (m, 5H), 2.88-2.97 (m, 1H), 6.68 (s, 1H), 7.11-7.16 (m, 1H), 7.17-7.29 (m, 4H); LCMS-MS (ESI+) 256.0 (M+H); HPLC (UV=100%), (ELSD=100%).

Workup

  1. additionSilica gel was added
  2. customthe silica gel-imbedded material was purified by flash chromatography (0-80% EtOAc/Heptane)

Sources & evidence

ORD record
ord-51a3c2b763f545c6bcac166e07695632
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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