Potassium Carbonate → N-Boc-4-methyl-1-pentyn-3-amine

HRID 659136Notes

Reaction equation

HRID 659136 reaction equation
[CH3:1][CH:2]([CH3:14])[CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=O.[N+](=[C:17](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][CH:2]([CH3:14])[CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 545985Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate2×HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one2×

Product 1

HCID 16753880N-Boc-4-methyl-1-pentyn-3-amineYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.25 g of tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate (Formula 21) and 1.79 g of dimethyl 1-diazo-2-oxopropylphosphonate (Formula 15) in 80 mL of methanol at 0° C. was added 1.72 g of potassium carbonate. The mixture was stirred at room temperature for 16 hours then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Column chromatography (15% ethyl acetate/hexane) gave 1.01 g of tert-butyl 4-methylpent-1-yn-3-ylcarbamate (Formula 22) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 0.98-1.00 (m, 6H), 1.45 (s, 9H), 1.87-1.93 (m, 1H), 2.24-2.25 (m, 1H), 4.32 (br, 1H).

Workup

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81bcd1dc393843fca3db3006e0291496
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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