Sodium Bicarbonate → (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-ol

HRID 1859004Notes

Reaction equation

HRID 1859004 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH:11]=[C:12]2[C@H:18]([CH3:21])[CH2:19][OH:20])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>C(OC(=O)C)C.[Pd]>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]2[C@H:18]([CH3:21])[CH2:19][OH:20])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 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-ol

Product 1

HCID 21309368(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propan-1-olYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.27 g (6.7 mMol) of (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 in 22.7 ml of ethylacetate were added 227 mg of Pd/C 10% and 227 mg of sodium bicarbonate. The reaction mixture was stirred under hydrogen atmosphere overnight, filtered over Speedex using ethylacetate for washing thoroughly and the solvent evaporated in vacuo. The residue was chromatographed over a 250 g Lobar column with hexane/ethylacetate 9/1 to yield 2.18 g (95.5%) of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphtalen-1-yl]-propan-1-ol as an oily product.

Workup

  1. filtrationfiltered over Speedex
  2. washfor washing thoroughly
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed over a 250 g Lobar column with hexane/ethylacetate 9/1

Sources & evidence

ORD record
ord-79098df518bc46bdbc7303e078399e5b
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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