[2-(2-Hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol → 1-{2-[4-(8-Methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidine

HRID 916864ノート

反応式

HRID 916864 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[CH:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)[OH:22]>Cl.C1COCC1.O>[CH3:20][O:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]3[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[CH2:2][O:22][CH:21]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]5[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]5)=[CH:27][CH:28]=4)[C:10]3=2)[CH:15]=1

参加物

5

反応物 1

HCID 17987053[2-(2-Hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol

生成物 1

HCID 589615531-{2-[4-(8-Methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidine収率 64%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Add several drops of HCl (5M) to a stirred solution of crude [2-(2-hydroxymethyl-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanol in THF (5 mL) and water (0.5 mL). Stir at r.t. for 24 h. Quench with aq. NaHCO3 and dilute with CH2Cl2. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-5% (2M NH3/MeOH) in CH2Cl2) to yield 1-{2-[4-(8-methoxy-11,13-dihydro-12-oxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-11-yl)-phenoxy]-ethyl}-piperidine (105 mg, 64%).

後処理

  1. customQuench with aq. NaHCO3
  2. additiondilute with CH2Cl2
  3. washWash the organic phase with water and brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude product by flash chromatography (0-5% (2M NH3/MeOH) in CH2Cl2)

出典と根拠

ORDレコード
ord-7eab8a486c2f496a96fb06e8310251c6
出典データセット
uspto-grants-2007_09
特許番号
US07271264B2

反応ノート

読み込み中…