Hydrogen Peroxide → methyl 6-(2-hydroxycyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008988Notes

Reaction equation

HRID 1008988 reaction equation
[C:1]1([C:7]2[C:8]3[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:9]=3[NH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-].[Na+].OO.C([O-])(O)=[O:24].[Na+]>C1COCC1>[OH:24][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[C:7]1[C:8]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][C:9]=2[NH:10][CH:11]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67298542methyl 6-cyclohex-1-en-1-yl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298624methyl 6-(2-hydroxycyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2M solution in THF of borane dimethylsulfide complex (1.5 eq.) was added at 0° C. to a 0.1M solution of methyl 6-cyclohex-1-en-1-yl-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry THF, and the mixture was stirred at RT for 7 h. After cooling to 0° C., the mixture was treated with 3M aq. NaOH (3 eq.) and 35% hydrogen peroxide (4 eq.). The mixture was allowed to warm to RT overnight. Aq. NaHCO3-solution was added and the mixture was extracted with EtOAc; the organic layer was washed with water and brine, dried over Na2SO4 and concentrated. Chromatography (PE/EtOAc) afforded the title compound (56%). 1H-NMR (300 MHz, CDCl3, 300 K, δ) 8.30 (bs, 1H), 7.68 (s, 1H), 7.08 (d, 1H, J 2.0), 3.89 (s, 3H), 3.70-3.65 (m, 1H), 2.58-2.49 (m, 1H), 2.16-2.12 (m, 1H), 1.98-1.65 (m, 4H), 1.47-1.23 (m, 3H); MS (ES+) m/z 280 (M+H)+.

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperatureto warm to RT overnight
  3. extractionthe mixture was extracted with EtOAc
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4086d62fc605473e99f3b3fc30450346
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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