Diallyl ether → HCID 131725707, compound

HRID 1796792Notes

Reaction equation

HRID 1796792 reaction equation
[CH2:1]([N:4]([CH:22]([C:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:29][SiH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:23]([OH:27])(C)[CH:24]=C)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].C(OCC=C)C=C>C=CC1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl.C(Cl)Cl>[CH2:15]([O:14][C:11]1[CH:10]=[CH:9][C:8]([S:5]([N:4]2[CH2:1][CH:2]=[CH:3][C:23]([CH3:24])([OH:27])[CH:22]2[C:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[O:29][SiH2:30][C:31]([CH3:32])([CH3:33])[CH3:34])(=[O:6])=[O:7])=[CH:13][CH:12]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 11194Diallyl etherHCID 131725705HCID 131725705, compound2×

Product 1

HCID 131725707HCID 131725707, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-allyl-4-benzyloxy-N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-2-methyl-but-3-enyl]-benzenesulfonamide (compound of formula VII, 4.0 g, 6.1 mmol), diallyl ether (0.82 ml, 0.66 g, 6.7 mmol), bis(tricyclohexylphosphine)benzylidine ruthenium (IV) dichloride (0.34 g, 0.4 mmol) and methylene chloride (116 ml) was stirred at reflux for about 3 hours. The mixture was concentrated in vacuo then purified using a Flash 40 system (silica gel cartridge, eluting with 10% ethyl acetate in hexane) to afford 2.8 g of 1-(4-benzyloxy-benzenesulfonyl)-2-(tert-butyldiphenyl-silanyloxymethyl)-3-methyl-1,2,3,6-tetrahydro-pyridin-3-ol (compound of formula VIII) as a colorless solid.

Workup

  1. temperatureat reflux for about 3 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthen purified
  4. washa Flash 40 system (silica gel cartridge, eluting with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-031c4c069fec42f4b5205fdb9910d14b
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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