Hydrochloric Acid → (3r,4r)-2-Methylene-3-[(3s)-3-tert-butyldimethylsiloxy-5-phenylpent-1-ynyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one

HRID 1018818노트

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HRID 1018818 반응식
[O:1]([C@@H:9]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]#[CH:11])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C([Li])CCC.[Cl-].C([Al+]CC)C.C(N([CH2:36][C:37]1[C:38](=[O:50])[CH2:39][C@@H:40]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH:41]=1)CC)C.[Cl-].[NH4+].Cl>CCCCCC.C1(C)C=CC=CC=1>[CH2:36]=[C:37]1[C@@H:41]([C:11]#[C:10][C@@H:9]([O:1][Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3])[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:40]([O:42][Si:43]([C:46]([CH3:48])([CH3:47])[CH3:49])([CH3:44])[CH3:45])[CH2:39][C:38]1=[O:50]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 10424731(4R)-2-(N,N-diethylamino)methyl-4-(tert-butyldimethylsiloxy)cyclopent-2-en-1-oneHCID 16686102Diethyl aluminum chlorideHCID 25257491(3s)-3-(Tert-butyldimethylsiloxy)-5-phenyl-1-pentyneHCID 178418339Butyllithium

생성물 1

HCID 22899370(3r,4r)-2-Methylene-3-[(3s)-3-tert-butyldimethylsiloxy-5-phenylpent-1-ynyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

실험 절차

To a toluene solution (22 ml) of (3S)-3-(tert-butyldimethylsiloxy)-5-phenyl-1-pentyne (1.96 g) was added n-butyl lithium (2.5 M, hexane solution, 2.64 ml) at 0° C., followed by stirring at room temperature for 30 minutes. To the solution was added diethylaluminum chloride (0.95 N, hexane solution, 8.10 ml) at 0° C., followed by stirring at room temperature for 30 minutes. To the solution was added (4R)-2-(N,N-diethylamino)methyl-4-(tert-butyldimethylsiloxy)cyclopent-2-en-1-one (0.25 M, toluene solution, 22.0 ml) at room temperature, followed by stirring for 15 minutes. The reaction solution was poured into a mixture of hexane (53 ml), a saturated aqueous ammonium chloride solution (53 ml) and an aqueous hydrochloric acid solution (3 N, 15.4 ml) with stirring, and the organic layer was separated and washed with a saturated aqueous sodium bicarbonate solution (20 ml). The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated, and the resulting residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=49:1) to give (3R,4R)-2-methylene-3-[(3S)-3-tert-butyldimethylsiloxy-5-phenylpent-1-ynyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one (1.65 g).

후처리

  1. stirringby stirring at room temperature for 30 minutes
  2. stirringby stirring for 15 minutes
  3. customthe organic layer was separated
  4. washwashed with a saturated aqueous sodium bicarbonate solution (20 ml)
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe resulting residue was purified by a silica gel column chromatography (developing solvent; hexane:ethyl acetate=49:1)

출처 및 근거

ORD 기록
ord-db6113cb0c6d488faafe8ddc68c13392
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482990B1

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