Lithium Hydroxide → HCID 59180049, compound

HRID 601877Notes

Reaction equation

HRID 601877 reaction equation
O1CCCC1[C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[CH2:9][CH:10]1[C:17]2[CH:16]=[C:15]([C:18]([O:20]C)=[O:19])[NH:14][C:13]=2[CH2:12][CH2:11]1.[OH-].[Li+].[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[O:30]1[CH2:31][CH2:27][CH:28]([C:6]2[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=2)[CH2:9][CH:10]2[C:17]3[CH:16]=[C:15]([C:18]([OH:20])=[O:19])[NH:14][C:13]=3[CH2:12][CH2:11]2)[CH2:29]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66873799HCID 66873799, compound

Product 1

HCID 59180049HCID 59180049, compound

Procedure

The title compound was synthesized from methyl 4-(3-(tetrahydrofuran-2-yl)benzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.028 g, 0.086 mmol) and lithium hydroxide (0.036 g, 0.86 mmol in 0.75 mL water), according to General Procedure 7. THF (0.75 mL) was used to solubilize the starting material. The resulting product was purified by reverse phase HPLC, eluting with a gradient of 40-100% MeOH: water (with 0.1% formic acid) to afford the title compound: 11 mg, 41% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.71-1.83 (m, 1H), 1.96-2.06 (m, 2H), 2.07-2.14 (m, 1H), 2.27-2.36 (m, 1H), 2.49-2.63 (m, 3H), 2.69-2.83 (m, 2H), 3.21-3.28 (m, 1H), 3.87-3.93 (q, 1H), 4.04-4.09 (q, 1H), 4.82-4.83 (m, 1H), 6.26-6.36 (d, 1H), 7.09-7.11 (m, 2H), 7.14-7.18 (m, 1H), 7.21-7.26 (m, 1H); LCMS-MS (ESI−) 310.2 (M−H); HPLC (UV=98.99%).

Workup

  1. customThe resulting product was purified by reverse phase HPLC
  2. washeluting with a gradient of 40-100% MeOH

Sources & evidence

ORD record
ord-eca7be48516a4bf495590904c09b9258
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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