Potassium Carbonate → HCID 86731568, compound

HRID 1430582Notes

Reaction equation

HRID 1430582 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C@H:13]([CH3:14])[CH2:12][CH2:11][C@@H:10]([CH:15]=O)[CH2:9]2)=[CH:5][CH:4]=1.[C:19](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:15]([C@H:10]1[CH2:9][N:8]([CH2:7][C:6]2[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C@H:13]([CH3:14])[CH2:12][CH2:11]1)#[CH:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86731566HCID 86731566, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86731568HCID 86731568, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (3R,6R)-1-(4-methoxybenzyl)-6-methylpiperidine-3-carbaldehyde (3.01 g, 12.2 mmol) and potassium carbonate (3.36 g, 24.3 mmol) in MeOH (150 mL) was treated with dimethyl (1-diazo-2-oxopropyl)phosphonate (2.19 mL, 14.6 mmol) and allowed to stir at ambient temperature for 3 d. The reaction was concentrated in vacuo and the residue taken up in sated, aqu. NaHCO3 and extracted twice with EtOAc. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo, providing (2R,5S)-5-ethynyl-1-(4-methoxybenzyl)-2-methylpiperidine as an orange oil. The material gave a mass ion (ES+) of 244.2 for M+H+. 1H NMR δ (ppm) (CDCl3): 7.21 (2H, dm J=8.4 Hz), 6.83-6.87 (2H, m), 3.98 (2H, d, J=13.4 Hz), 3.80 (3H, s), 3.11 (1H, d, J=13.6 Hz), 3.11 (1H, s), 2.91-2.96 (1H, m), 2.39-2.44 (1H, m), 2.18-2.25 (1H, m), 1.89-1.98 (2H, m), 1.64-1.69 (2H, m), 1.31-1.40 (2H, m), 1.18 (3H, d, J=6.0 Hz).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionNaHCO3 and extracted twice with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db35a5327d234456982ea26818c646e0
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

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