Lithium Hydroxide → HCID 59180110, compound

HRID 601848Notes

Reaction equation

HRID 601848 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH:4]1[C:11]2[CH:10]=[C:9]([C:12]([O:14]C)=[O:13])[NH:8][C:7]=2[CH2:6][CH2:5]1.[OH-].[Li+]>>[F:17][C:2]([F:1])([F:16])[CH2:3][CH:4]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[NH:8][C:7]=2[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 59180235HCID 59180235, compound

Product 1

HCID 59180110HCID 59180110, compound

Procedure

The title compound was synthesized from methyl 4-(2,2,2-trifluoroethyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.2888 g, 1.2 mmol, 1 equiv) and lithium hydroxide (1.1 mL, 2 M aqueous, 5.3 equiv) according to General Procedure 7. The resulting product was purified by preparative HPLC (using the Chromeleon purification system (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 50% methanol and increasing to 100% over 7 minutes)) to afford the title compound. 60.2 mg, (63%), with purity by HPLC of 98.9% (UV). LCMS m/e 232 (M−H). 19F NMR (376 MHz, METHANOL-d4) δ ppm −66.50 (t, J=9.94 Hz, 3F). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.05-2.17 (m, 1H), 2.19-2.33 (m, 1H), 2.44 (ddd, J=14.88, 11.45, 6.56 Hz, 1H), 2.59-2.83 (m, 3H), 3.23 (quin, J=6.79 Hz, 1H), 6.65 (s, 1H).

Workup

  1. customThe resulting product was purified by preparative HPLC (
  2. customthe Chromeleon purification system (0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase)
  3. temperatureincreasing to 100% over 7 minutes))

Sources & evidence

ORD record
ord-b64fbc6abc3947b08fa39b5a11843ae2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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