7,7-Dioxo-5,6-dihydrothieno[2,3-b]thiopyran-4-one → (R)-(+)-5,6-Dihydro-4H-thieno[2,3-b]-thiopyran-4-ol-7,7-dioxide

HRID 2082451

반응식

HRID 2082451 반응식
[S:1]1[C:5]2[S:6](=[O:12])(=[O:11])[CH2:7][CH2:8][C:9](=[O:10])[C:4]=2[CH:3]=[CH:2]1.C1(C(C2C=CC=CC=2)([C@@H]2CCCN2)O)C=CC=CC=1.B.CSC.B>C1COCC1>[S:1]1[C:5]2[S:6](=[O:12])(=[O:11])[CH2:7][CH2:8][C@@H:9]([OH:10])[C:4]=2[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 36139597,7-Dioxo-5,6-dihydrothieno[2,3-b]thiopyran-4-oneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 178419238HCID 178419238, 화합물

생성물 1

HCID 1480164(R)-(+)-5,6-Dihydro-4H-thieno[2,3-b]-thiopyran-4-ol-7,7-dioxide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-15 °C

실험 절차

To a magnetically stirred solution of 5,6-Dihydro-4H-thieno[2,3-b]-thiopyran-4-one-7,7-dioxide (13) (1.00 g, 4.94 mmol) in dry THF (14 mL) was added (S)-diphenylprolinol-borane complex from Example 12 (132 mg, 0.494 mmol). The solution was cooled to -15° C. and a solution of borane-dimethyl sulfide (10M, 0.4 mL, 4.0 mmol) in dry THF (6.8 mL) was added at a rate to maintain the internal temperature at -15° C. The solution was stirred at -15° C. for 1 hour then at 22° C. for 6 hours. The product was isolated by the method decribed in Example 34 Step E. The enantiomeric ratio of the purified product was 95:5.

후처리

  1. temperatureto maintain the internal temperature at -15° C
  2. waitat 22° C. for 6 hours
  3. customThe product was isolated by the method

출처 및 근거

ORD 기록
ord-e941b227db9e492291cf9d5d1feca6a1
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05189177

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