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 2248436

Reaktionsgleichung

Reaktionsgleichung von HRID 2248436
[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@]2(CO)CCCN2C2C=CC=CC=2)C=CC=CC=1.C1(C(C2C=CC=CC=2)([C@@H]2CCCN2)O)C=CC=CC=1.B.B.CSC>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

Komponenten

6

Edukt 4

HCID 36139597,7-Dioxo-5,6-dihydrothieno[2,3-b]thiopyran-4-oneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 53249241(S)-DiphenylprolinolHCID 178419238HCID 178419238, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a magnetically stirred solution of 5,6-Dihydro-4H-thieno[2,3-b]-thiopyran-4-one-7,7-dioxide (9) (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-methyl 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5abd2ed7764e4483af0149dcc4d2517c
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05039802

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