4-Bromophenol → 4-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

HRID 423473

反応式

HRID 423473 の反応式
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].[Br:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:16][CH2:15][CH:12]2[CH2:13][CH2:14][N:9]([C:7]3[O:6][N:5]=[C:4]([CH:2]([CH3:1])[CH3:3])[N:8]=3)[CH2:10][CH2:11]2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57930076{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol

生成物 1

HCID 666732104-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine収率 42.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (322 mg, 42%) was prepared from {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 450 mg, 2.0 mmol), 4-bromophenol (346 mg, 2.0 mmol) and Ph3P (629 mg, 2.4 mmol) in THF (5 mL) followed by diisopropyl azodicarboxylate (0.512 mL, 2.6 mmol) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 2H, J=9.1 Hz), 6.76 (d, 2H, J=8.9 Hz), 4.28-4.18 (m, 2H), 3.79 (d, 2H, J=6.2 Hz), 3.14-3.04 (m, 2H), 2.94-2.82 (m, 1H), 2.10-1.94 (m, 1H), 1.97-1.87 (m, 2H), 1.49-1.36 (m, 2H), 1.28 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 380/382 (M+H).

出典と根拠

ORDレコード
ord-e373751943234688bcd1de3b473fc837
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

関連ノート

読み込み中…