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4-Vinylpyridine → N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine

HRID 2252990
ノート
印刷プレビュー

反応式

HRID 2252990 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]O)[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:30]1[CH2:35][CH2:34]O[C@H:32]([CH2:36][C:37]2C=CC=C(Br)C=2)[CH2:31]1)(OC(C)(C)C)=O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(C1C=CN=CC=1)=C.C(N(CC)CC)C>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:37][C:36]3[CH:32]=[CH:31][N:30]=[CH:35][CH:34]=3)[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 67073062N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholineHCID 67073309N-Boc-(R)-2-(3-bromobenzyl)morpholine

生成物 1

HCID 67073377N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine
収率 57%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
140 °C

実験手順

Intermediate (b) N-Boc-(R)-2-(3-bromobenzyl)morpholine (103 mg, 0.29 mmol), was dissolved in CH3CN (2 mL) with palladium acetate (3.2 mg, 14 umol), tris(ortho-tolyl)phosphine (8.8 mg, 29 umol), 4-vinylpyridine (61 mg, 0.58 mmol) and triethyl amine (58 mg, 0.58 mmol). The reaction was then subjected to microwave heating at 140° C. for 5 minutes. The reaction was cooled to room temperature, partitioned between ethyl acetate (20 mL) and water (20 mL) and separated. The organic layer was washed with brine (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica; 20-30% ethyl acetate/isohexane) to yield the desired intermediate (a), N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine as a colorless gum (63 mg, 57%).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between ethyl acetate (20 mL) and water (20 mL)
  3. customseparated
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica; 20-30% ethyl acetate/isohexane)

出典と根拠

ORDレコード
ord-6f0aa0debdd94eefa1094fae778462a7
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07323466B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート