Triethylamine → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

HRID 462799노트

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HRID 462799 반응식
[Si:1]([O:8][CH:9]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)/[CH:10]=[CH:11]/[CH:12]1[CH2:19][CH2:18][CH:17]2[CH:13]1[CH2:14][CH:15]([C:21]([OH:31])([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:22])[C:16]2=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38]S(Cl)(=O)=O.C(N(CC)CC)C.N12CCCN=C1CCCCC2>C1C=CC=CC=1.O>[Si:1]([O:8][CH:9]([CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)/[CH:10]=[CH:11]/[CH:12]1[CH2:19][CH2:18][CH:17]2[CH:13]1[CH2:14][CH:15]([C:21]1([OH:31])[CH2:22][CH2:38][CH:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:23]1)[C:16]2=[O:20])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2].[CH:17]12[CH2:18][CH2:19][CH2:12][CH:13]1[CH2:14][CH2:15][C:16]2=[O:20]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 203972076-[(E)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-(5-ethoxycarbonyl-2-hydroxypent-2-yl)bicyclo[3,3,0]octan-2-one

생성물 2

HCID 1406313,3a,4,5,6,6a-hexahydro-2H-pentalen-1-oneHCID 13241022(E)-6-(3-tert-Butyldimethylsilyloxy-3-cyclohexylprop-1-enyl)-3-(4-ethoxycarbonyl-1-hydroxycyclohex-1-yl)bicyclo[3,3,0]octan-2-one

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

A stirred solution of 6-[(E)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-(5-ethoxycarbonyl-2-hydroxypent-2-yl)bicyclo[3,3,0]octan-2-one (26 mg), prepared as described in Reference Example 39 and in the form of 6β-[(E)-3β-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-(5-ethoxycarbonyl-2-hydroxypent-2-yl)bicyclo[3,3,0]octan-2-one, otherwise known as (±)-ethyl(13E)-(9S,15R)-6a-oxo-6,9-methano-15-tert-butyldimethylsilyloxy-15-cyclohexyl-5-hydroxy-5-methyl-16,17,18,19,20-pentanorprost-13-enoate, in benzene (0.19 ml) was treated with methanesulphonyl chloride (0.0048 ml) at the ambient temperature, followed by triethylamine (0.008 ml) and the mixture was stirred for 2 hours. It was then treated with 1,8-diazabicyclo[5,4,0]undec-7-ene (0.0446 ml) and the mixture was stirred for 2 hours. It was then treated with water (10 ml) and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under reduced pressure. The resulting residue was subjected to medium pressure, short column chromatography on silica gel, using a mixture of ethyl acetate and hexane (1:8 v/v) as eluant, to give 6-[(E)-3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-{[mixture of (E) and (Z)]-5-ethoxycarbonylpentylid-2-ene}bicyclo[3,3,0]octan-2-one (22 mg), in the form of (±)-6β-[(E)-3β-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-3-{[mixture of (E) and (Z)]-5-ethoxycarbonylpentylid-2-ene}bicyclo[3,3,0]octan-2-one, otherwise known as (±)-ethyl [mixture of (5E and (5Z)],(13E)-(9S,15R)-6a-oxo-6,9-methano-5-methyl-15-tert-butyldimethylsilyloxy-15-cyclohexyl-16,17,18,19,20-pentanorprosta-5,13-dienoate.

후처리

  1. stirringthe mixture was stirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. additiona mixture of ethyl acetate and hexane (1:8 v/v) as eluant

출처 및 근거

ORD 기록
ord-3e219d7097b84d41874fe24592df190b
출처 데이터셋
uspto-grants-1985_05
특허 번호
US04517202

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