Methyl morpholine oxide → 4-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

HRID 1795167Notes

Reaction equation

HRID 1795167 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)([CH:14]=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 11000987HCID 11000987, compound

Product 1

HCID 219368754-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-cyclohexyl-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester, 3, (1.0 g, 3.36 mmol), 4-methylmorpholine N-oxide (0.54 g, 4.64 mmol), and molecular sieves (0.5 g) in methylene chloride (20 mL) under argon atmosphere is added tetrapropylammonium perruthenate (35.5 mg) at room temperature. The mixture is stirred for 30 min to 1 hour after which the solution is filtered through a pad of silica and the solvent removed in vacuo to afford the desired product as a colorless oil, which is used without further purification. MS (ESI) m/z 318, (M+Na+).

Workup

  1. filtrationis filtered through a pad of silica
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4f176b99a0b74b3e9288f7a212f2ff19
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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