Potassium Carbonate → HCID 86009475, compound

HRID 2212092Notes

Reaction equation

HRID 2212092 reaction equation
[C:1]1([S:7]([C:10]([CH3:26])([CH3:25])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20](OCC)=O)[CH2:16][CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[CH2:28]([Al+]CC(C)C)C(C)C.[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]1([S:7]([C:10]([CH3:25])([CH3:26])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]#[CH:28])[CH2:16][CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21225700DiisobutylaluminumhydrideHCID 69663779HCID 69663779, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86009475HCID 86009475, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(4-Benzenesulfonyl-4-methylpentyl)-4-ethoxycarbonylpiperidine (0.3 g, 0.79 mmol) was dissolved in dichloromethane (5 ml) and cooled to −78° C. Diisobutylaluminium hydride (1.0M in dichloromethane, 1.0 ml, 1.0 mmol) was added. The reaction was stirred for 30 minutes at −78° C. then quenched by the addition of ethyl acetate (0.5 ml) and water (0.1 ml). The mixture was stirred at room temperature for 10 minutes then filtered through Celite. The filtrate was concentrated in vacuo. The residue was dissolved in methanol (20 ml). Dimethyl (1-diazo-2-oxopropyl)phosphonate (0.3 g, 1.56 mmol) and potassium carbonate (0.23 g, 1.65 mmol) were added and the reaction stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 2–4% methanol/dichloromethane, to give the title compound (90 mg, 34%). NMR of hydrochloride salt:

Workup

  1. customthen quenched by the addition of ethyl acetate (0.5 ml) and water (0.1 ml)
  2. stirringThe mixture was stirred at room temperature for 10 minutes
  3. filtrationthen filtered through Celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in methanol (20 ml)
  6. stirringthe reaction stirred at room temperature for 1 hour
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe residue partitioned between ethyl acetate and brine
  9. dry with materialThe organic layer was dried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography on silica gel
  12. washeluting with 2–4% methanol/dichloromethane

Sources & evidence

ORD record
ord-96b4e142c0b54ec6a450fb95fcedb6a0
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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