Methyl morpholine oxide → benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-oxohexan-2-yl](3-methylbutyl)carbamate

HRID 1524348Notes

Reaction equation

HRID 1524348 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[N:10]([C@@H:16]([CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([O:8][C:9](=[O:41])[N:10]([C@@H:16]([CH2:36][CH2:37][CH2:38][CH:39]=[O:40])[CH2:17][O:18][Si:19]([C:32]([CH3:33])([CH3:34])[CH3:35])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86708050benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-hydroxyhexan-2-yl](3-methylbutyl)carbamate

Product 1

HCID 86708051benzyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}-6-oxohexan-2-yl](3-methylbutyl)carbamate

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the material from Step 6 (3.27 g, 5.68 mmol) in dichloromethane (57 mL) were added 4-methylmorpholine N-oxide (0.8 g, 6.81 mmol), and activated 4 Å molecular sieves. After stirring at room temperature for 10 minutes, TPAP (0.1 g, 0.28 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 3 hours, and then filtered through a silica gel plug. The filtrate was concentrated in vacuo to afford the title compound which was used directly at Step 8.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. filtrationfiltered through a silica gel plug
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8299bb8a969e4d2f96dc942e86203660
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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