Methyl morpholine oxide → (S)-tert-butyl 4-oxo-2-(((triisopropylsilyl)oxy)methyl)piperidine-1-carboxylate

HRID 1522017Notes

Reaction equation

HRID 1522017 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:4]([CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH2:3]1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:4]([CH2:15][O:16][Si:17]([CH:18]([CH3:20])[CH3:19])([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:25])[CH3:26])[CH2:3]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 90412138(2S)-tert-butyl 4-hydroxy-2-(((triisopropylsilyl)oxy)methyl)piperidine-1-carboxylate

Product 1

HCID 90412108(S)-tert-butyl 4-oxo-2-(((triisopropylsilyl)oxy)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 260B (3.32 g, 8.56 mmol) in dichloromethane (28.5 mL) was added activated powdered 4 Å molecular sieves (9 g), tetrapropylammonium perruthenate (0.150 g, 0.428 mmol) and N-methylmorpholine-N-oxide (1.505 g, 12.85 mmol), and the mixture was stirred overnight at room temperature. The mixture was filtered through a pad of silica, rinsing with ethyl acetate. The filtrate was concentrated and purified by flash chromatography on silica gel (gradient from 0-20% ethyl acetate-heptanes) to give the title compound. MS (ESI+) m/z 385.8 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica
  2. washrinsing with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography on silica gel (gradient from 0-20% ethyl acetate-heptanes)

Sources & evidence

ORD record
ord-34d6f5d593834a3387a25f2073c70cdb
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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