Methyl iodide → HCID 59778587, compound

HRID 655963Notes

Reaction equation

HRID 655963 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:22]I>CN(C=O)C>[Si:3]([O:10][CH2:11][C@@H:12]([N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11858590HCID 11858590, compound

Product 1

HCID 59778587HCID 59778587, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (60% dispersed in mineral oil, 60 mg, 1.49 mmol, 1.15 equiv.) in DMF (2.0 mL) was added (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (360 mg, 1.3 mmol). The reaction mixture was stirred for 30 min followed by addition of methyl iodide (93 μL, 1.49 mmol, 1.15 equiv.) and stirred for 1 h. LC/MS indicated the reaction was complete. The reaction mixture was quenched with saturated NH4Cl and diluted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)propan-2-yl(methyl)carbamate as an oil, which was used in the next step without further purification. LRMS (M-Boc+H+) m/z 204.1.

Workup

  1. stirringstirred for 1 h
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. additiondiluted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb869b6ffe974720a6a6e774e7f68042
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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