Potassium Carbonate → 5,6-Dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 30251ノート

反応式

HRID 30251 の反応式
C([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].ClC(OC(Cl)C)=O>ClC(Cl)C.CO>[Br:20][C:17]1[S:16][C:13]2[CH:14]3[CH:10]([CH2:11][C:12]=2[C:18]=1[Br:19])[CH2:9][NH:8][CH2:15]3

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 5213051-Chloroethyl chloroformateHCID 1317270302-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

生成物 1

HCID 597894515,6-Dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
22 °C

実験手順

The product from step g) (605 mg, 1.46 mmol) in dichloroethane (7 ml) was treated with powdered K2CO3 (806 mg, 5.84 mmol) and 1-chloroethyl chloroformate (Ace-Cl) (632 μl, 5.84 mmol) at 80° C. for 16 hours. Next, the reaction was cooled, filtered and concentrated providing an oily residue. This oily residue was diluted with anhydrous MeOH (15 ml) and stirred for 1 hour at 22° C. The solvent was concentrated and the crude residue was purified by preparative LC/MS providing title compound. 1H NMR (300 MHz, CD3OD, ppm) 2.65-2.75 (m, 1H); 3.05-3.30 (m, 2H); 3.32-3.80 (m, 4H); 4.10-4.28 (br m, 1H); MS calculated for C9H9Br2NS+H 324, observed 322, 324, 326.

後処理

  1. temperatureNext, the reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customproviding an oily residue
  5. concentrationThe solvent was concentrated
  6. customthe crude residue was purified by preparative LC/MS

出典と根拠

ORDレコード
ord-b2ba5165d1ec4365a3717803667ac969
出典データセット
uspto-grants-2008_09
特許番号
US07423056B2

反応ノート

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