Methyl iodide → HCID 56637742, compound

HRID 1638574Notes

Reaction equation

HRID 1638574 reaction equation
[C:1]([NH:8][C@H:9]([CH2:14][OH:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16][Si]([N-][Si](C)(C)C)(C)C.[Li+].CI>O1CCCC1>[CH3:16][O:15][CH2:14][C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 7018766Boc-L-leucinol

Product 1

HCID 56637742HCID 56637742, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 463 mg (2.43 mmol) of BOC-leucinol in 2 ml of tetrahydrofuran at -78° C. under argon is added 2.4 mL (2.4 mmol) of a 1 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran. After 10 minutes, 0.3 ml (4.8 mmol) of methyliodide was added and the resulting mixture is allowed to warm to room temperature. It is then heated to reflux for 1 hour and then cooled. The mixture is partitioned between 40 ml of dichloromethane and 30 ml portions of dichloromethane. The combined residue is chromatographed on silica gel with 15% ethyl acetate in hexane to give 405 mg (1.75 mmol, 83%) of BOC-leucinol methyl ether. 1H-NMR (CDCl3): δ0.9 d (d, d×3H, J=6 Hz), 1.44, 3.33.

Workup

  1. temperatureIt is then heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. customThe mixture is partitioned between 40 ml of dichloromethane and 30 ml portions of dichloromethane
  5. customThe combined residue is chromatographed on silica gel with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-31fd395baa96464bac306807434be658
Source dataset
uspto-grants-1989_11
Patent number
US04880781

Reaction notes

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