Methanol → HCID 59180185, compound

HRID 601858Notes

Reaction equation

HRID 601858 reaction equation
[Br: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.[OH-].[Li+].CO>C1COCC1>[Br: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

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180070HCID 59180070, compound

Product 1

HCID 59180185HCID 59180185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(4-bromobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.0998 g, 0.3 mmol, 1 equiv) and lithium hydroxide (0.8 mL, 2 M aqueous, 1.6 mmol, 5.3 equiv), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (5 mL) was used. The resulting product was purified via preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 70% methanol and increasing to 100% over 7 minutes) afforded the title compound. 67.2 mg, with purity by HPLC of 100% (UV). LCMS m/e 318 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.02-2.16 (m, 1H), 2.49-2.67 (m, 3H), 2.74 (dd, J=9.77, 7.37 Hz, 2H), 3.19-3.29 (m, 1H), 6.29 (s, 1H), 7.11 (d, J=8.35 Hz, 2H), 7.41 (q, J=4.25 Hz, 2H).

Workup

  1. customThe resulting product was purified via preparative HPLC
  2. customthe Chromeleon purification system
  3. temperatureincreasing to 100% over 7 minutes)

Sources & evidence

ORD record
ord-f09a7145ad4b41208f8467f6acca0e8d
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…