Dimethyl Sulfoxide → 1-Boc-piperidine-3-carboxaldehyde

HRID 704395Notes

Reaction equation

HRID 704395 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][OH:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH:24]=[O:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehydeYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulfoxide (0.85 ml) was added to a solution of 0.50 ml of oxalyl chloride in 10 ml of dichloromethane at -60° C. and, 3 minutes later, a solution of 1.08 g of 1-tert-butoxycarbonylpiperidine-3-methanol in 10 ml of dichloromethane was added dropwise over 5 minutes. After stirring for 15 minutes, 3.0 ml of triethylamine was added to the reaction mixture. After further 5 minutes of stirring, water (20 ml) was added to the reaction mixture and, after shaking, the dichloromethane layer was separated. The dichloromethane layer was washed with 1N hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride in that order, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 0.98 g of 1-tert-butoxycarbonylpiperidine-3-carbaldehyde.

Workup

  1. stirringAfter further 5 minutes of stirring
  2. stirringafter shaking
  3. customthe dichloromethane layer was separated
  4. washThe dichloromethane layer was washed with 1N hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-920127c3c4664342964af3781bf903db
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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