Hydrochloric Acid → Triapenthenol

HRID 1383078

반응식

HRID 1383078 반응식
[CH:1]1([CH:7]=[C:8]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCCC1>[CH:1]1(/[CH:7]=[C:8](/[N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)\[CH:9]([OH:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 566097071-Cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one

생성물 1

HCID 6437842Triapenthenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

29 ml (0.029 mol) of boron hydride-tetrahydrofuran complex are added to a solution of 4.1 g (0.0145 mol) of S-2-(dibenzyl-hydroxymethyl)-pyrrolidine in 30 ml of absolute tetrahydrofuran at 20° C., with stirring. After the mixture has been stirred at 20° C. for 30 minutes, 2.61 g (0.01 mol) of the (E)-isomer of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-one are added and the mixture is stirred at 40° C. for a further 16 hours. Thereafter, the reaction mixture is poured into 100 ml of 2N aqueous hydrochloric acid. The mixture formed is extracted twice with methylene chloride and the combined organic phases are concentrated under reduced pressure. The residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel. 2.3 g (87% of theory) of the (-)-antipode of (E)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ene are obtained in this manner in the form of a crystalline product.

후처리

  1. stirringAfter the mixture has been stirred at 20° C. for 30 minutes
  2. stirringthe mixture is stirred at 40° C. for a further 16 hours
  3. customThe mixture formed
  4. extractionis extracted twice with methylene chloride
  5. concentrationthe combined organic phases are concentrated under reduced pressure
  6. customThe residue which remains is chromatographed with a mixture of chloroform/ethyl acetate=4:1 on silica gel

출처 및 근거

ORD 기록
ord-76b4ef37dcf64d44a09ae318e295ba63
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808725

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