Methyl iodide → HCID 11644978, 화합물

HRID 916347노트

반응식

HRID 916347 반응식
[O:1]=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[CH3:22][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>C1COCC1>[CH3:22][CH:8]1[C:2](=[O:1])[CH2:3][CH:4]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:7]1[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile

생성물 1

HCID 11644978HCID 11644978, 화합물수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 156AF03-217 (552 mg, 2 mmol) in THF (20 mL) under argon atmosphere at −78° C. was added dropwise lithium bis(trimethylsilyl)amide (2.6 mL, 2.6 mmol, 1 M in THF). After 30 min at −78° C., iodomethane (2.0 mL) was added over 1 min and the reaction was allowed to warm to rt overnight. Partitioning of the reaction mixture between ethyl acetate (2×500 mL) and water (500 mL), drying of the combined organic phases over Na2SO4, filtration, removing of volatiles in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted) afforded the title compound (115 mg, 20%) as a thick oil.

후처리

  1. customPartitioning of the reaction mixture between ethyl acetate (2×500 mL) and water (500 mL)
  2. dry with materialdrying of the combined organic phases over Na2SO4, filtration
  3. customremoving of volatiles in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted)

출처 및 근거

ORD 기록
ord-27e89e45ffd949da9e8f56773ad492c6
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268232B2

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