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 1075553Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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 silica gel 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.

Workup

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

Sources & evidence

ORD record: ord-c9ecf53cbb604effb591475f756fba45
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905074

Reaction notes

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