Methanol → HCID 59180181, compound

HRID 601862Notes

Reaction equation

HRID 601862 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1.[OH-].[Li+].CO>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH:6]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[NH:10][C:9]=2[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59180089HCID 59180089, compound

Product 1

HCID 59180181HCID 59180181, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3-methylbenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (85 mg, 0.31 mmol) and lithium hydroxide (129 mg, 3.10 mmol in 3 mL water), according to General Procedure 7. A 1:1 mixture of methanol (MeOH) and THF (6 mL) was used. The resulting product was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 50% EtOAc to afford the title compound. 45 mg, 57% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.07-2.20 (m, J=12.57, 8.44, 6.21, 6.21 Hz, 1H), 2.35 (s, 3H), 2.50-2.84 (m, 5H), 3.26-3.35 (m, 1H), 6.53 (d, J=1.42 Hz, 1H), 6.98-7.07 (m, 2H), 7.17-7.22 (m, 1H), 7.23-7.34 (m, 1H), 8.84 (br. s., 1H). LCMS m/e 256 (M+H). Purity ˜100% (HPLC).

Workup

  1. customThe resulting product was purified by chromatography
  2. washeluting with heptane-EtOAc, gradient 0 to 50% EtOAc

Sources & evidence

ORD record
ord-b2a2daeb76b4464b91a5d1e04c1935db
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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