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

HRID 592546Notes

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

Conditions

Temperature: 75 °C

Procedure

A 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 107a (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 (room temperature), 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 107b.

Workup

customA 250-mL single neck round bottomed flask equipped with a magnetic stirrer and nitrogen inlet
additionwere added
customthe organic layer was separated
extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-f706b2e002a74839a9d59571ca3e3988
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

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