Water → ETHYL 5,5-DIMETHYL-1,4,5,6-TETRAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLATE

HRID 1918922Notes

Reaction equation

HRID 1918922 reaction equation
Cl[C:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH2:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12].[N-:16]=[N+]=[N-].[Na+].O.C(Cl)Cl>CS(C)=O>[CH3:7][C:5]1([CH3:8])[CH2:6][C:2]2[NH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:3]=2[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 33557Sodium AzideHCID 86661240HCID 86661240, compound

Product 1

HCID 68096415ETHYL 5,5-DIMETHYL-1,4,5,6-TETRAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLATEYield 37.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 167a (17 g, 74 mmol) in DMSO (100 mL). To the solution was added sodium azide (9.6 g, 150 mmol). The mixture was then heated to 75° C. and stirred for 8 h. After cooling to rt, H2O (100 mL) and CH2Cl2 (200 mL) were added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using a 100% hexane-1:1 hexane/ethyl acetate gradient to afford a 37% yield (5.7 g) of 167b.

Workup

  1. customA 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. temperatureAfter cooling to rt
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-abd39d1167c64ac4a353396d4f3b9a66
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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