Methyl iodide → Methyl 2-[3-[(tert-Butoxycarbonyl)(methyl)amino]-2,2-dimethylpropoxy]-4-tert-butylbenzoate

HRID 644287Notes

Reaction equation

HRID 644287 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:28])([CH3:27])[CH2:11][O:12][C:13]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CI.[CH3:31][Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.ClCCl>[C:1]([O:5][C:6]([N:8]([CH3:31])[CH2:9][C:10]([CH3:28])([CH3:27])[CH2:11][O:12][C:13]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68530988Methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate

Product 1

HCID 68533360Methyl 2-[3-[(tert-Butoxycarbonyl)(methyl)amino]-2,2-dimethylpropoxy]-4-tert-butylbenzoateYield 61.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-tert-butylbenzoate (2.50 g, 6.35 mmol) in THF at 0° C. under N2 was added methyl iodide (4.51 g, 31.8 mmol, 5 eq), followed by sodium bis(trimethylsilyl)amide (12.7 mL, 12.7 mmol, 1.0 M in THF). The cooling bath was allowed to slowly warm to room temperature. The reaction was stirred at room temerature for 2.5 days, then diluted with dichloromethane, washed with water and brine, dried, and concentrated in vacuo to give 1.60 g (61.8%) of the desired product as a viscous oil which was used without further purification.

Workup

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9caf840ea0e49a6b017fa59e264757d
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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