Triphenylphosphine → 1-(3-Methylpyridin-2-yl)ethan-1-amine

반응식

[N:1]([CH:4]([C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:5])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH3:12][C:11]1[C:6]([CH:4]([NH2:1])[CH3:5])=[N:7][CH:8]=[CH:9][CH:10]=1

참가 물질

실험 절차

A solution of the above azide (254 mg, 1.57 mmol) and PPh3 (828 mg, 3.16 mmol) in 10% aqueous THF (10 mL) was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (CH2Cl2/MeOH, 9:1), giving 1-(3-methyl-pyridin-2-yl)-ethylamine as a yellow liquid (163 mg, 1.20 mmol, 76%). 1H NMR (CDCl3) δ 1.35 (d, 3H, J=6.6 Hz), 2.00 (s, 2H), 2.33 (s, 3H), 4.30 (q, 1H, J=6.6 Hz), 7.05 (dd, 1H, J=7.5, 4.8 Hz), 7.40 (d, 1H, J=7.5 Hz), 8.41 (d, 1H, J=4.2 Hz).

후처리

customThe solvent was removed under reduced pressure
customthe residue was purified by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

출처 및 근거

ORD 기록: ord-42f4fc2f483f43a8a59379c75068d1df
출처 데이터셋: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07291631B2

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참가 물질

반응물 2

HCID 11776Triphenylphosphine

HCID 914713542-(1-Azido-ethyl)-3-methyl-pyridine

생성물 1

HCID 457911661-(3-Methylpyridin-2-yl)ethan-1-amine수율 76.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

후처리

customThe solvent was removed under reduced pressure
customthe residue was purified by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

출처 및 근거

ORD 기록: ord-42f4fc2f483f43a8a59379c75068d1df
출처 데이터셋: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07291631B2

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