Methyl morpholine oxide → tert-Butyl 2-formylpiperidine-1-carboxylate

HRID 899728Notes

Reaction equation

HRID 899728 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][OH:15])=[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[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH:14]=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 2763853N-Boc-piperidine-2-methanol

Product 1

HCID 10656219tert-Butyl 2-formylpiperidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.737 g, 3.4 mmol) in dry CH2Cl2 (10 mL) was added 3 Å molecular sieves (1.03 g), N-methylmorpholine N-oxide (0.644 g, 5.5 mmol), and tetrapropylammonium perruthenate (72 mg, 0.21 mmol) and the mixture stirred at room temperature for 3 h. The reaction mixture was purified through a silica gel plug (Hexanes/EtOAc, 70:30 followed by 100:0) to afford the title aldehyde (0.500 g, 70%) as a pale yellow oil.

Workup

  1. customThe reaction mixture was purified through a silica gel plug (Hexanes/EtOAc, 70:30 followed by 100:0)

Sources & evidence

ORD record
ord-ab822dd12a654e8784d1c79e4782a3b9
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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