Methyl iodide → HCID 67493879, compound

HRID 1921923Notes

Reaction equation

HRID 1921923 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:11]1[CH2:24][C:25]#[CH:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:27]([Li])CCC.IC>C1COCC1>[CH2:24]([C@H:11]1[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:14][C:13]([CH3:15])([CH3:16])[N:12]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:25]#[C:26][CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 86627012HCID 86627012, compoundHCID 178418339Butyllithium

Product 1

HCID 67493879HCID 67493879, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of (4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-(prop-2-ynyl)oxazolidine-3-carboxylate (0.60 g, 1.6 mmol) in THF (5 mL) was cooled to −78° C. and butyllithium (0.75 mL, 1.9 mmol) was added dropwise. After 5 min, the mixture was re-cooled to −78° C. and iodomethane (0.15 mL, 2.3 mmol) was added dropwise. The mixture was stirred at 0° C. for 2 h and brought to RT and stirred for 15 h. The reaction mixture was quenched with sat NH4Cl, filtered, concentrated, and chromatographed on silica gel eluting with hexanes to afford a light yellow oil as (4S,5S)-tert-butyl 4-(but-2-ynyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.463 g, 74% yield). MS m/z: 298 (M+1).

Workup

  1. custombrought to RT
  2. stirringstirred for 15 h
  3. customThe reaction mixture was quenched with sat NH4Cl
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-ad2a5b309f1340a1ba2bca290efb633e
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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