Methyl iodide → HCID 58124946, compound

HRID 1971696Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[H][H].[CH3:27]I>CN(C=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([N:15]([CH3:27])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:13])[CH3:14])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 750 mg of 12b in 4 ml of DMF was treated with 200 mg of 60% NaH (dispersion in mineral oil) and heated under N2 at 50° C. for 10 min, after which time evolution of hydrogen gas ceased. The reaction mixture was cooled to 0° C. and 500 μl of methyl iodide was added. The reaction mixture was stirred for an additional 2 hr and quenched by pouring into ice-water (caution excess NaH). The product was extracted with ethyl acetate and the extract was washed with water, dried, concentrated and the crude material was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 550 mg of 12c as colorless oil; Rf 0.50 (heptane/ethyl acetate 3/1). NMR (CDCl3) δ 0.05 (s, 6, Si(CH3)2), 0.89 (s, 9, tertC4H9Si), 1.32 (s, 6, C(CH3)2) 1.42 (s, 9, tertC4H9+m, 2, CH2), 1.72 (m, 2, CH2), 2.88 (s, 3, NCH3), 3.60 t, 2, CH2).

Workup

temperatureThe reaction mixture was cooled to 0° C.
customquenched
additionby pouring into ice-water (caution excess NaH)
extractionThe product was extracted with ethyl acetate
washthe extract was washed with water
customdried
concentrationconcentrated
customthe crude material was purified by chromatography over silica gel

Sources & evidence

ORD record: ord-4a58f0de76564fd5b4d78ee902d35f7e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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