HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1075554
Notes
Print preview

Reaction equation

HRID 1075554 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938PalladiumCatalyst
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 2.27 g (6.7mMol) 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-1f46db00402d42679b7cba3b4207a9eb
Source dataset
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05905074

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes