Sodium Methoxide → 6-Methoxy-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 30252Notes

Reaction equation

HRID 30252 reaction equation
C(OC([N:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3[C:16](Br)=[CH:15][S:14][C:11]=32)[CH2:7]1)=O)C.[CH3:18][O-:19].[Na+]>CO.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][O:19][C:16]1[C:10]2[CH2:9][CH:8]3[CH:12]([C:11]=2[S:14][CH:15]=1)[CH2:13][NH:6][CH2:7]3

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 1317270316-Bromo-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

Product 1

HCID 597894596-Methoxy-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent2×

Procedure

The product of step b) (57.8 mg, 0.183 mmol) in MeOH (51 μl) was treated with CuO (7 mg, 0.09 mmol), a 25% solution of sodium methoxide in MeOH (129 μl) and tetra-butylammonium iodide (TBAI) (10 mg) at 100° C. for 12 hours. The reaction mixture was cooled and purified by preparative LC/MS to give the title compound. 1H NMR (300 MHz, CDCl3, ppm) 2.40-2.60 (m, 1H); 2.82-3.01 (m, 2H); 3.05-3.63 (br m, 4H); 3.77 (s, 3H); 3.81-3.98 (br s, 1H); 6.17 (s, 1H); MS calculated for C10H13NOS+H 196, observed 196.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-78650246e50849b182f0a801d847290d
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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