Methanol → HCID 86671311, compound

HRID 1472889Notes

Reaction equation

HRID 1472889 reaction equation
[CH3:1][CH:2]([CH3:14])[C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=[O:5].[CH3:15][Mg]Br.CO.[NH4+].[Cl-]>C1COCC1>[OH:5][CH:4]([C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:2]([CH3:14])[CH3:1])[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 11830471106391-88-2HCID 178418573HCID 178418573, compound

Product 1

HCID 86671311HCID 86671311, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate (2.5 g, 12.42 mmol) was dissolved in THF (50 mL) and cooled to 0° C. Methyl magnesium bromide (17.0 mL, 51.0 mmol, 3.0 M in diethyl ether) was carefully added via syringe. The reaction was allowed to warm to ambient temperature and left stirring overnight. The cloudy mixture was chilled to 0° C., quenched with methanol (3.0 mL, 74.0 mmol), followed by the addition of 200 mL saturated NH4Cl solution, and extracted twice with 200 mL MTBE. The organic phase was washed with 200 mL brine, dried over Na2SO4, filtered, and concentrated to provide the title compound (2.484 g, 11.43 mmol, 92% yield) as a yellow oil. MS (DCI+) m/z 218.1 (M+H).

Workup

  1. temperatureto warm to ambient temperature
  2. waitleft
  3. temperatureThe cloudy mixture was chilled to 0° C.
  4. extractionextracted twice with 200 mL MTBE
  5. washThe organic phase was washed with 200 mL brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8e4c888bea98421b9f7fcb7396eafa16
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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