Potassium Carbonate → 4,5,6,7,7a,8-Hexahydro-3bH-1-thia-5-aza-cyclopenta[alpha]indene

HRID 30273Notes

Reaction equation

C([N:8]1[CH2:16][CH:15]2[CH:11]([CH2:12][C:13]3[S:19][CH:18]=[CH:17][C:14]=32)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CC(Cl)OC(Cl)=O>ClC(Cl)C>[S:19]1[C:13]2[CH2:12][CH:11]3[CH:15]([C:14]=2[CH:17]=[CH:18]1)[CH2:16][NH:8][CH2:9][CH2:10]3

Participants

Conditions

Temperature: 22 °C

Procedure

The product from step g) (963 mg, 3.58 mmol) in dichloroethane (18 ml) was treated with K2CO3 (1.97 g, 14.3 mmol) and Ace-Cl (1.54 ml, 14.3 mmol) at 80° C. for 16 hours. Next, the reaction mixture was filtered, concentrated and the residue was dissolved in anhydrous MeOH (25 ml) and stirred for 1 h at 22° C. The MeOH was concentrated and triturated with ether to give 467 mg (61%) of the subtitle compound. MS calculated for C10H13NS+H 180, observed 180.

Workup

filtrationNext, the reaction mixture was filtered
concentrationconcentrated
dissolutionthe residue was dissolved in anhydrous MeOH (25 ml)
concentrationThe MeOH was concentrated
customtriturated with ether

Sources & evidence

ORD record: ord-ef4fca7745fa46aa8999547abfab36bb
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423056B2

Reaction notes

Loading…