Potassium Carbonate → HCID 117702551, compound

HRID 1503256Notes

Reaction equation

HRID 1503256 reaction equation
[CH:1]([C:3]12[CH2:10][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)=O.[C:19]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].C([O-])(O)=O.[Na+]>CO.C(OCC)(=O)C>[C:1]([C:3]12[CH2:10][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)#[CH:19]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 117702617HCID 117702617, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 117702551HCID 117702551, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-formylbicyclo[3.2.1]octan-1-ylcarbamate (6.4 g, 25.3 mmol) and K2CO3 (7.1 g, 50.6 mmol) in methanol (200 mL) under N2 was added dimethyl 1-diazo-2-oxopropylphosphonate (6.0 g, 30.3 mmol). After stirring at room temperature for three hours, the reaction mixture became a clear solution. Ethyl acetate (300 mL) and 5% NaHCO3 (300 mL) were added. Aqueous layer was extracted with ethyl acetate (2×200 mL). The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 5.8 g (90%) the crude title compound, tert-butyl 5-ethynylbicyclo[3.2.1]octan-1-ylcarbamate, as colorless oil. ESI-MS m/z: 194 (M-55)+.

Workup

  1. extractionAqueous layer was extracted with ethyl acetate (2×200 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8185649645234025825fd88e3e2e1977
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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