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Triethylamine → Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

HRID 471032
ノート
印刷プレビュー

反応式

HRID 471032 の反応式
FC(F)(F)C(O)=O.[O:8]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C:19]([C:21]2[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=2)=[O:20])[CH2:10][CH2:9]1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][OH:40])[CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>C(#N)C>[OH:40][CH2:39][CH2:38][C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][N:16]1[CH2:17][CH2:18][C:13]2([O:8][CH2:9][CH2:10][N:11]([C:19]([C:21]3[S:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH:22]=3)=[O:20])[CH2:12]2)[CH2:14][CH2:15]1
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

5

反応物 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67292236Methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate

生成物 1

HCID 57989150Methyl 5-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒

反応条件

温度
20 °C

実験手順

A solution of methyl 5-(1-oxa-4,9-diazaspiro[5.5]undecane-4-carbonyl)thiophene-2-carboxylate trifluoroacetate (example 30, step b) (0.46 g) and 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.226 g) in acetonitrile (10 mL) was treated with triethylamine (0.44 mL) and the mixture stirred at 20° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 1% triethylamine and 3% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.41 g.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-1b04b597b15f4200869e22e5b71dd5d7
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629271B2

反応ノート

読み込み中…

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