Piperidine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-[4-(1-piperidinocarbonylmethoxy)phenyl]ethynyl)cyclohexane

HRID 343569

反応式

HRID 343569 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[CH:26])[CH2:20][CH2:19][C:18]4([O:24][CH2:23][CH2:22][O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO[C:29](=[O:39])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35](I)=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:59]1[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:35]4[CH:34]=[CH:33][C:32]([O:31][CH2:30][C:29]([N:59]5[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]5)=[O:39])=[CH:37][CH:36]=4)[CH2:20][CH2:19][C:18]4([O:21][CH2:22][CH2:23][O:24]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 6457537methyl 2-(4-iodophenoxy)acetateHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

生成物 1

HCID 700813064-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-[4-(1-piperidinocarbonylmethoxy)phenyl]ethynyl)cyclohexane収率 96%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

A stirred mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.150 g, 0.42 mmol) and 4-iodophenoxyacetic acid methyl ester (0.123 g, 0.42 mmol) in dry piperidine (2 mL) was treated at 80° C. for 1.5 hr by the procedure of Example 11 with a mixture of tetrakis(triphenylphosphine)palladium (0.027 g, 0.023 mmol), cuprous iodide (0.0048 g, 0.025 mmol), and triphenylphosphine (crystal). The crude product was chromatographed (silica 50 to 75% ethyl acetate in petroleum ether) and was stripped in vacuo to afford the titled intermediate as a viscous yellow oil (0.232 g, 96%). 1H-NMR (400 MHz, CDCl3) δ 7.38 (d, J=8.7 Hz, 2H), 7.24 (d, J=2.3 Hz, 1H), 7.13 (d-d, J=8.4 Hz, J=2.3 Hz, 1H), 6.89 (d, J=8.9, 1H), 6.84 (d, J=8.4, 1H),4.81 (p, 1H), 4.69 (s, 2H), 4.00 (s, 4H), 3.84 (s, 3H), 3.56 (t, J=5.5 Hz, 2H), 3.49 (t, J=5.5 Hz, 2H), 2.3 to 1.5 (m, 32H with H2O).

後処理

  1. customThe crude product was chromatographed (silica 50 to 75% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-670a34c34d514118a9667a565fd45d23
出典データセット
uspto-grants-1999_01
特許番号
US05861421

関連ノート

読み込み中…