Triphenylphosphine → HCID 54063657、化合物

HRID 843140

反応式

HRID 843140 の反応式
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:14]3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:26][OH:27].[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39](O)=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39]([O:27][CH2:26][C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]5[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]6[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=6)[CH2:14]5)[C:6]=4[C:2]=3[CH3:1])=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylateHCID 54356540[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol

生成物 1

HCID 54063657HCID 54063657、化合物収率 29.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol (107 mg), 5-hydroxybenzofuran-2-carboxylic acid ethyl ester (60 mg), triphenylphosphine (100 mg) and azodicarboxylic acid diethyl ester (70 μl) were dissolved in THF (7 ml). The solution was stirred overnight at room temperature. A white precipitate separated out. The precipitate was filtered out and the filtrate was evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 5-[3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-ylmethoxy]-benzofuran-2-carboxylic acid ethyl ester (48 mg) as a colorless oil. FAB-MS: m/z 555 (MH+); 1H-NMR (CDCl3): δ 1.25-2.23 (7H, m), 1.43 (3H, t, J=7 Hz), 2.24 (3H, s), 2.78 (1H, m), 2.95 (1H, m), 3.47 (1H, d, J=13 Hz), 3.57 (1H, d, J=13 Hz), 3.89 (2H, m), 4.44 (2H, q, J=7 Hz), 5.10 (2H, s), 6.55 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.14 (1H, dd, J1=9 Hz, J2=2 Hz), 7.23 (3H, m), 7.47 (1H, m), 7.48 (1H, s), 7.66 (1H, br d, J=7 Hz), 8.48 (1H, br d, J=5 Hz), 8.53 (1H, br s).

後処理

  1. customA white precipitate separated out
  2. filtrationThe precipitate was filtered out
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was separated by silica gel column chromatography

出典と根拠

ORDレコード
ord-f785f2041a364ae988fe6080d199f080
出典データセット
uspto-grants-2002_04
特許番号
US06376491B1

関連ノート

読み込み中…