Potassium Carbonate → HCID 117702591, compound

HRID 1503264Notes

Reaction equation

HRID 1503264 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([CH:18]=O)([CH2:11]3)[CH2:9]1)[CH2:15]2)([CH3:4])([CH3:3])[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:18]([C:10]12[CH2:16][CH:14]3[CH2:13][CH:12]([CH2:17][C:8]([NH:7][C:6](=[O:20])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])([CH2:15]3)[CH2:9]1)[CH2:11]2)#[CH:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117717162HCID 117717162, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 117702591HCID 117702591, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl-3-formyl-1-adamantylcarbamate (600 mg, 2.1 mmol) and K2CO3 (590 mg, 4.2 mmol) in methanol (60 mL) under N2 atmosphere was added dimethyl (1-diazo-2-oxopropyl)phosphonate (490 mg, 2.5 mmol). After stirring at room temperature for three hours the clear reaction solution was partitioned between ethyl acetate (100 mL) and 5% NaHCO3 (100 mL) and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 600 mg (100%) of the title compound, tert-butyl 3-ethynyl-1-adamantylcarbamate as a colorless oil. ESI-MS m/z: 220 (M-55)+.

Workup

  1. customwas partitioned between ethyl acetate (100 mL) and 5% NaHCO3 (100 mL)
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e0b6efa8c5345dca3c8007c604fd04c
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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