Potassium Carbonate → Tert-butyl 4-ethynyl-4-methylpiperidine-1-carboxylate

HRID 1471771Notes

Reaction equation

HRID 1471771 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([CH:21]=O)([CH3:20])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([C:21]#[CH:1])([CH3:20])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22248051tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 72207605Tert-butyl 4-ethynyl-4-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (5.25 g) and 4-formyl-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (5.23 g) are added to an ice cold mixture of dimethyl (1-diazo-2-oxopropyl)-phosphonate (5.50 g), molecular sieves (2 g), and methanol (30 mL). The mixture is stirred in the cooling bath for 30 min and then at room temperature overnight. The mixture is filtered and aqueous NH4Cl solution is added to the filtrate. The resulting mixture is extracted with dichloromethane and the combined extracts are concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the title compound.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe mixture is filtered
  4. additionaqueous NH4Cl solution is added to the filtrate
  5. extractionThe resulting mixture is extracted with dichloromethane
  6. concentrationthe combined extracts are concentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-d7061bffdd994d02831f7920b8f15c9f
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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