Methanol → 4-(Naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 601869Notes

Reaction equation

HRID 601869 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]1[C:19]2[CH:18]=[C:17]([C:20]([O:22]C)=[O:21])[NH:16][C:15]=2[CH2:14][CH2:13]1.[OH-].[Li+].CO>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]1[C:19]2[CH:18]=[C:17]([C:20]([OH:22])=[O:21])[NH:16][C:15]=2[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180124Methyl 4-(naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 591801624-(Naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(naphthalen-2-ylmethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.104 g, 0.34 mmol) and lithium hydroxide (0.148 g, 3.53 mmol in 5 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (10 mL) was used. The solvent was removed under reduced pressure, and the residue re-dissolved in ca. 5 mL H2O and acidified to pH 7 with 1 N HCl. The solids formed were collected, affording the title compound as a light pink solid: 77 mg, 76% yield. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.16 (ddt, J=12.34, 8.74, 5.98, 5.98 Hz, 1H), 2.50-2.76 (m, 3H), 2.92-3.03 (m, 2H), 3.37-3.47 (m, 1H), 6.31 (d, J=1.71 Hz, 1H), 7.41-7.50 (m, 3H), 7.73 (s, 1H), 7.82-7.90 (m, 3H), 10.39 (br. s, 1H); LCMS-MS (ESI−) 290.0 (M−H); HPLC (UV=93.55%), (ELSD=100%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue re-dissolved in ca. 5 mL H2O
  3. customThe solids formed
  4. customwere collected

Sources & evidence

ORD record
ord-c99c6d9d2bab4a21a1326fb3f38e2c29
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…