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Water → 8beta-(Tert-butyldimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline

HRID 547956
ノート
印刷プレビュー

反応式

HRID 547956 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:13]([CH3:14])[CH2:12]1.C(N(CC)CC)C.O>CN(C)C=O>[O:9]([CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:13]([CH3:14])[CH2:12]1)[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 14987LysergolHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 598415568beta-(Tert-butyldimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline収率 96.6%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Tert-butyldimethylsilyl chloride (TBS-Cl, 19.6 g) is added into a mixture of Lysergol (30 g) and triethylamine (16.7 g) in N,N-dimethylformamide (150 mL) and the mixture is stirred at room temperature for 2-3 h. The mixture is cooled and water (240 mL) is added. The resulting suspension is stirred for an additional 2 h and then filtered and washed with water. The product is dried under vacuum to give 42 g of 8β-(tert-butyldimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline in 96.5% yield.

後処理

  1. temperatureThe mixture is cooled
  2. stirringThe resulting suspension is stirred for an additional 2 h
  3. filtrationfiltered
  4. washwashed with water
  5. customThe product is dried under vacuum

出典と根拠

ORDレコード
ord-52a40d20c789440bb37639adfcd824c3
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07939665B2

反応ノート

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