Methyl iodide → HCID 57791175, compound

HRID 1944716Notes

Reaction equation

HRID 1944716 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Na+].[CH3:21]I>C1COCC1>[CH3:21][O:1][CH2:2][CH2:3][C@@H:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7016521tert-Butyl [(1R)-3-hydroxy-1-phenylpropyl]carbamate2×

Product 1

HCID 57791175HCID 57791175, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-tert-Butyl 3-hydroxy-1-phenylpropylcarbamate (Intermediate 60, 258 mg, 1.03 mmol) was dissolved in THF under nitrogen at 0° C. NaH was added and the reaction mixture was stirred at 0° C. for 10 min. MeI was added and the reaction mixture was stirred at room temperature for 30 min. then quenched with sat. aq. Na2SO4 and extracted with Et2O. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified via column chromatography using a biotage SP1 25+M column with a gradient 50% EtOAc in heptane calculated from TLC. Product fractions were combined and concentrated to give the title compound as a white solid (78 mg, 29%). LCMS=[M+H]=266

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 30 min.
  2. customthen quenched with sat. aq. Na2SO4
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via column chromatography
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4415569a1e7f415aaf5f599f37665c81
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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