Potassium Iodide → 6-Cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene

HRID 397319Notes

Reaction equation

[H-].[Na+].[CH2:3]1[C:7]2=[CH:8][C:9]3[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH:24]1(Br)[CH2:26][CH2:25]1>CS(C)=O.O>[CH:24]1([O:15][C:11]2[CH:12]=[CH:13][C:14]3[N:6]4[CH2:5][CH2:4][CH2:3][C:7]4=[CH:8][C:9]=3[CH:10]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

6.00 g sodium hydride 55-65% in oil in portion was added during ca 30 min at room temperature to a solution of 23.5 g 2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-6-ol in 200 mL dimethylsulfoxide. 18.75 g potassium carbonate and 1.700 g potassium iodide and 34 mL cyclopropylbromide was added to the resulting solution. The resulting suspension was stirred under argon at 100° C. for 48 h. Another 17 mL cyclopropylbromide was added. The resulting suspension was stirred under argon at 100° C. for 24 h. The reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was purified by chromatography on silica gel with hexane:dichloromethane=1:1 to yield 17.75 g 6-Cyclopropoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene as a white crystalline solid melting at 61-63° C.

Workup

stirringThe resulting suspension was stirred under argon at 100° C. for 24 h
extractionextracted with dichloromethane
customThe organic phase was purified by chromatography on silica gel with hexane

Sources & evidence

ORD record: ord-ba10ba55ed994f879172e7479da81d00
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610685B2

Reaction notes

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