Tetrapropylammonium → HCID 86754886, compound

HRID 1604834Notes

Reaction equation

HRID 1604834 reaction equation
C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC.[OH:22][C:23]([CH3:44])([CH3:43])/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[CH2:28][C@H:29]([C@H:31]1[CH2:40][CH2:39][CH2:38][C@@H:37]2[C@:32]1([CH3:42])[CH2:33][CH2:34][CH2:35][C@@H:36]2O)[CH3:30]>C(Cl)Cl>[OH:22][C:23]([CH3:43])([CH3:44])/[CH:24]=[CH:25]/[CH:26]=[CH:27]/[CH2:28][C@H:29]([C@H:31]1[CH2:40][CH2:39][CH2:38][C@@H:37]2[C@@:32]1([CH3:42])[CH2:33][CH2:34][CH2:35][CH2:36]2)[CH3:30]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 86754884HCID 86754884, compound

Product 1

HCID 86754886HCID 86754886, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

459 mg of 4-methylmorpholine N-oxide, 40 mg of tetrapropylammonium perrhutenate, and 2.53 g of molecular sieves (powder, 4Å) were stirred for 0.25 h at ambient temperature. 590 mg of (1S,4aR,5R,8aR)-5-[(3E,5E )-(R)-(7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)]-4a-methyl-decahydro-naphthalen-1-ol, dissolved in 5 ml of CH2Cl2, was added and the mixture kept for 2.5 h at RT. Dilution with ether, filtration over SiO2, evaporation and flash chromatography (SiO2, hexane/AcOEt=7/3) afforded 283 mg of (4aR,5R,8aR)-5-[(3E,5E)-(R)-(7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen]-1-one besides of 166 mg of a mixture of product and starting alcohol.

Workup

  1. additionwas added
  2. filtrationDilution with ether, filtration
  3. customover SiO2, evaporation and flash chromatography (SiO2, hexane/AcOEt=7/3)

Sources & evidence

ORD record
ord-2f60746bcc8e4d1c8f767d2f8d22b81a
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

Loading…