Methyl morpholine oxide → 17-Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'-oxo-ethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

HRID 865596Notes

Reaction equation

HRID 865596 reaction equation
C([CH:3]1[CH2:29][CH2:28][CH2:27][CH:26]2[N:4]1[C:5](=[O:72])[C:6](=[O:71])[C:7]1([OH:70])[O:66][CH:11]([CH:12]([O:64][CH3:65])[CH2:13][CH:14]([CH3:63])[CH2:15][C:16]([CH3:62])=[CH:17][CH2:18][C:19](=[O:61])[CH2:20][CH:21]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH:22]([CH3:52])[CH:23]([C:31]([CH3:51])=[CH:32][CH:33]3[CH2:38][CH2:37][CH:36]([O:39][CH2:40][CH:41]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[OH:42])[CH:35]([O:49][CH3:50])[CH2:34]3)[O:24][C:25]2=[O:30])[CH:10]([O:67][CH3:68])[CH2:9][CH:8]1[CH3:69])C.C[N+]1([O-])CCO[CH2:76][CH2:75]1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:75]([CH:18]1[CH:17]=[C:16]([CH3:62])[CH2:15][CH:14]([CH3:63])[CH2:13][CH:12]([O:64][CH3:65])[CH:11]2[O:66][C:7]([OH:70])([CH:8]([CH3:69])[CH2:9][CH:10]2[O:67][CH3:68])[C:6](=[O:71])[C:5](=[O:72])[N:4]2[CH:26]([CH2:27][CH2:28][CH2:29][CH2:3]2)[C:25](=[O:30])[O:24][CH:23]([C:31]([CH3:51])=[CH:32][CH:33]2[CH2:38][CH2:37][CH:36]([O:39][CH2:40][C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:42])[CH:35]([O:49][CH3:50])[CH2:34]2)[CH:22]([CH3:52])[CH:21]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:55])[CH3:56])[CH2:20][C:19]1=[O:61])[CH3:76]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 57015410Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'hydroxyethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

Product 1

HCID 5712063917-Ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'-oxo-ethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraoneYield 77.1%

Reagents, catalysts & solvents 1

HCID 178419074HCID 178419074, compoundCatalyst

Procedure

To solution of 17 ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(2"'-phenyl-2"'hydroxyethyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (13 mg in 0.3 mL methylene chloride) was added powdered 4A molecular sieves (10 mg), 4-methylmorpholine N-oxide (6.0 mg), tetrapropylammonium perruthenate (1.0 mg) and the reaction stirred at room temperature. After 30 minutes the mixture was filtered through a small diatomaceous earth/silica gel plug and the filtrate concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate:hexane (1:2)+1% methanol) gave the title compound (10 mg).

Workup

  1. filtrationAfter 30 minutes the mixture was filtered through a small diatomaceous earth/silica gel plug
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by flash chromatography on silica gel (ethyl acetate:hexane (1:2)+1% methanol)

Sources & evidence

ORD record
ord-edada6aabbcd4628b4cb02e652b6b013
Source dataset
uspto-grants-1996_10
Patent number
US05565560

Reaction notes

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