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Formaldehyde → (S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol

HRID 1859003
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HRID 1859003 반응식
[C:1]([Si:5]([O:8][C@@H:9]1[C@H:18]2[C@@:13]([CH3:21])([C:14](=CC)[CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11][CH2:10]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH2:22]=O.[Cl-].C[Al+]C.C([O:30][CH2:31][CH3:32])C>C1(C)C=CC=CC=1.CCCCCC>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][C@H:9]1[CH2:10][CH2:11][CH2:12][C@@:13]2([CH3:21])[C@H:18]1[CH2:17][CH2:16][CH:15]=[C:14]2[C@H:32]([CH3:22])[CH2:31][OH:30])([CH3:3])([CH3:4])[CH3:2]
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참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 3283Diethyl EtherHCID 16686359Dimethylalumanylium chlorideHCID 57178905(1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethyl-silane

생성물 1

HCID 21309369(S)-2-[(4aR,5S,8aS)-5-(tert-butyldimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-propan-1-ol수율 67.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a stirred solution of 3.11 g (10.1 mMol) of (1S,4aS,8aR)-tert-Butyl-(5-ethylidene-4a-methyl-decahydro-naphtalen-1-yloxy)-dimethylsilane in 125 ml of toluene are added 0.33 g (11.1 mMol) of finely powdered paraformaldehyde. The reaction mixture is cooled to 0° C. and 12.56 ml of a one molar solution of dimethylaluminumchloride in hexane are added and kept for one hour at this temperature. The reaction mixture is stirred at room temperature overnight, diluted with diethylether, washed with 1N HCl and with water, then dried over sodium sulfate and evaporated in vacuo. The residue is chromatographed over a medium pressure 250 g silicagel column with hexane/ethylacetate 9/1 to yield 2.31 g (67.5%) of pure (S)-2-[(4aR,5S,8aS)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphtalen-1-yl]-propan-1-ol as an oil. By running the reaction with BF3.Et2O in CH2Cl2 small amounts of the (R)-epimer, the starting material of Examples 31-33 can be isolated.

후처리

  1. washwashed with 1N HCl and with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue is chromatographed over a medium pressure 250 g silicagel column with hexane/ethylacetate 9/1

출처 및 근거

ORD 기록
ord-f6c9373108f94647ad4816c66240799c
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153605

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