Triphenylphosphine → 2-[1-(4-Pyridyl)piperidin-4-ylmethoxy]aniline

HRID 346673

反応式

HRID 346673 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(OC([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][O:14][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH2:22])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4935485N-Boc-2-aminophenolHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanol

生成物 1

HCID 210802922-[1-(4-Pyridyl)piperidin-4-ylmethoxy]aniline収率 236.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(4-pyridyl)piperidin-4-ylmethanol (357 mg) and 2-tert-butyloxycarbonylaminophenol (328 mg) in tetrahydrofuran (15 ml) was added triphenylphosphine (447 mg) followed by diethyl azodicarboxylate (0.27 ml). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated to a gum which was purified by column chromatography on silica eluting with methanol/dichloromethane (10:90) to give the tert-butyloxycarbonyl protected derivative of 2-[1-(4-pyridyl)piperidin-4-ylmethoxy]aniline (1.05 g);

後処理

  1. concentrationThe reaction mixture was concentrated to a gum which
  2. customwas purified by column chromatography on silica eluting with methanol/dichloromethane (10:90)

出典と根拠

ORDレコード
ord-d422d900877642118b1fc47c2f655ce1
出典データセット
uspto-grants-2007_02
特許番号
US07173025B1

関連ノート

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