Potassium Carbonate → tert-butyl N-(2-methylbut-3-yn-2-yl)carbamate

HRID 2221451Notes

Reaction equation

HRID 2221451 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([NH:14][C:15]([CH3:19])([CH3:18])[CH:16]=O)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>CO.C(OCC)C.[Cl-].[NH4+]>[C:7]([NH:14][C:15]([CH3:18])([C:16]#[CH:1])[CH3:19])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Product 1

HCID 10655060tert-butyl N-(2-methylbut-3-yn-2-yl)carbamateYield 97.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of dimethyl 1-diazo-2-oxopropyl phosphonate (see Ohira, S. Synth. Commun. 19, 561-564, (1989)) (2.97 g, 15.5 mmol) in methanol (50 ml) at 0° C. was added potassium carbonate (1.71 g, 12.4 mmol) and slowly a solution of N-Boc-2-amino-2-methyl-propionaldehyde (1.45 g, 7.74 mmol) in methanol (5 ml). The reaction mixture was stirred at 0-10° C. for additional 6 h, diluted with diethylether (˜150 ml) and with saturated aqueous ammonium chloride solution (150 ml). The organic layer was washed with saturated aqueous ammonium chloride solution (100 ml), water (100 ml), and finally with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography over silica gel using ethyl acetate/hexane (1/10) provided N-Boc-2-amino-2-methylbut-3-yne (1.38 g) as yellowish oil.

Workup

  1. washThe organic layer was washed with saturated aqueous ammonium chloride solution (100 ml), water (100 ml)
  2. dry with materialfinally with brine, dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography over silica gel

Sources & evidence

ORD record
ord-36bd0b4fd30945f2840560ae21dc89c7
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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