Methyl iodide → HCID 66833735, compound

HRID 579547Notes

Reaction equation

HRID 579547 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:21][CH2:22][CH2:23][CH2:24][B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)([CH2:17][CH2:18][CH:19]=[CH2:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:34]1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>C(OCC)C>[C:1]([O:5][C:6]([N:8]([CH3:34])[C:9]([CH2:21][CH2:22][CH2:23][CH2:24][B:25]1[O:26][C:27]([CH3:33])([CH3:32])[C:28]([CH3:31])([CH3:30])[O:29]1)([CH2:17][CH2:18][CH:19]=[CH2:20])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66833408HCID 66833408, compound

Product 1

HCID 66833735HCID 66833735, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

While under an atmosphere of argon, a solution of tert-butyl 2-(tert-butoxycarbonylamino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoate (1.35 g, 2.89 mmol) in freshly distilled (THF 5 mL) was cooled to 0° C. and treated with sodium bis(trimethylsilyl)amide (6 mL, 1.0 M in THF) under argon. After stirring for 10 min, iodomethane (2.04 g, 14.4 mmol) was added and the reaction was warmed to room temperature and stirred for 16 h. After being complete by TLC, the reaction mixture was cooled to 0° C., diluted with ethyl ether and washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-20% ethyl acetate in heptane with 0.5% triethylamine over 8 CV) gave tert-butyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoate as a colorless oil (1.27 g, 91%). Rf 0.35 (20% ethyl acetate in heptane). ESI MS found for C26H48BNO6 m/z [482.3 (M+1)].

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred for 16 h
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by MPLC (1-20% ethyl acetate in heptane with 0.5% triethylamine over 8 CV)

Sources & evidence

ORD record
ord-c75993078e9e4e2daa2cea0140af7361
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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