Potassium Carbonate → tert-Butyl 3-ethynylpiperidine-1-carboxylate

HRID 1521930Notes

Reaction equation

HRID 1521930 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=O.[C:16](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[CH:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99644481-Boc-piperidine-3-carboxaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 21963855tert-Butyl 3-ethynylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of Example 1C (2 g, 9.38 mmol) in methanol (20 mL) was added potassium carbonate (3.89 g, 28.1 mmol) and the mixture was stirred for 30 minutes. Dimethyl 1-diazo-2-oxopropylphosphonate (3.60 g, 18.76 mmol) was added and the mixture was stirred for 12 hours. The mixture was filtered through diatomaceous earth and concentrated to afford crude material which was purified by column chromatography (silica gel, 15% ethyl acetate in hexane) to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 1.41 (s, 9H), 1.55-1.59 (m, 1H), 1.67-1.69 (m, 2H), 1.96-1.99 (m, 1H), 2.06-2.07 (m, 1H), 2.43-2.44 (m, 1H), 2.93-3.02 (m, 2H), 3.69-3.75 (m, 1H), 3.9-4.0 (m, 1H).

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customto afford crude material which
  5. customwas purified by column chromatography (silica gel, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7f9d48fc3c4646b9b8255b6ca701a8a4
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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