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Ethyldiphenylphosphine → tert-butyl 3-(3-acetamido-3-(tert-butylcarbamoyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)heptyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 579535
ノート
印刷プレビュー

反応式

HRID 579535 の反応式
C1(P(CC)C2C=CC=CC=2)C=CC=CC=1.[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][BH:19][O:18]1.[C:25]([NH:28][C:29]([C:54](=[O:60])[NH:55][C:56]([CH3:59])([CH3:58])[CH3:57])([CH2:49][CH2:50][CH2:51][CH:52]=C)[CH2:30][CH2:31][CH:32]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][N:33]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])(=[O:27])[CH3:26]>ClCCl>[C:25]([NH:28][C:29]([C:54](=[O:60])[NH:55][C:56]([CH3:59])([CH3:58])[CH3:57])([CH2:49][CH2:50][CH2:51][CH2:52][B:19]1[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:24])([CH3:16])[O:18]1)[CH2:30][CH2:31][CH:32]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][N:33]1[C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])(=[O:27])[CH3:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 69082EthyldiphenylphosphineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 66833614tert-butyl 3-(3-acetamido-3-(tert-butylcarbamoyl)oct-7-enyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

生成物 1

HCID 66833409tert-butyl 3-(3-acetamido-3-(tert-butylcarbamoyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)heptyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

While under an atmosphere of argon, a solution of bis(1,5-dicyclooctadiene)diiridium(I) dichloride (54 mg, 3% mol), diphenylphosphinoethane (64 mg, 6% mol) and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 mL, 10.7 mmol) in dry dichloromethane (20 mL) was cooled to 0° C. A second solution of tert-butyl 3-(3-acetamido-3-(tert-butylcarbamoyl)oct-7-enyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.5 g, 2.67 mmol) in dry dichloromethane (20 mL) was added in one portion. After 4 h LCMS indicated all the starting olefin was consumed and the reaction was washed successively with water, sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated. Purification by flash chromatography (20-35% ethyl acetate in hexanes) gave tert-butyl 3-(3-acetamido-3-(tert-butylcarbamoyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)heptyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate as a yellow oil (1.5 g, 93%). ESI MS found for C34H56BN3O6 m/z [614.7 (M+1), 633.7 (M+23)].

後処理

  1. customall the starting olefin was consumed
  2. washthe reaction was washed successively with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (20-35% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-22e97bf785b24a649c4e2ce438dd3f1f
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040703B2

反応ノート

読み込み中…

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