Methanol → HCID 59180210, compound

HRID 601857Notes

Reaction equation

HRID 601857 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[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>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[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 59180198HCID 59180198, compound

Product 1

HCID 59180210HCID 59180210, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized from methyl 4-(3,4-dichlorobenzyl)-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.064 g, 0.2 mmol) and lithium hydroxide (0.084 g, 2.0 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 column chromatography (Isco CombiFlash) eluting with a gradient of 0-100% EtOAc/heptane to afford a light brown solid: 14 mg, 23% yield. 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.00-2.15 (m, 1H), 2.46-2.67 (m, 3H), 2.69-2.84 (m, 2H), 3.19-3.29 (m, 1H), 6.31 (s, 1H), 7.11 (dd, J=8.20, 2.00 Hz, 1H), 7.34 (d, J=1.95 Hz, 1H), 7.37-7.45 (m, 1H); HPLC (UV=96.1%), (ELSD=100%).

Workup

  1. customThe resulting product was purified by column chromatography (Isco CombiFlash)
  2. washeluting with a gradient of 0-100% EtOAc/heptane
  3. customto afford a light brown solid

Sources & evidence

ORD record
ord-3331058338024fccb122eacb8406495e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…