Methyl iodide → tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylate

HRID 1471770Notes

Reaction equation

HRID 1471770 reaction equation
[CH3:1]C(C)([O-])C.[K+].CI.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=[O:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>ClCCl.[Cl-].[Na+].O>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]([CH:22]=[O:23])([CH3:1])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22248051tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium tert-butoxide (2.80 g) and methyl iodide (3.60 mL) are added to an ice cold solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (4.00 g) in dichloromethane (24 mL). The mixture is stirred in the cooling bath for 30 min and then at room temperature overnight. Brine is added and the resulting mixture is extracted with dichloromethane. The combined extracts are dried (MgSO4) and concentrated to give the crude title compound that is used without further purification.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe resulting mixture is extracted with dichloromethane
  4. dry with materialThe combined extracts are dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7aa62cebefb94e4cb8685a33c6f7f770
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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