(R)-beta-aminophenethyl alcohol → HCID 90025824、化合物

HRID 59690

反応式

HRID 59690 の反応式
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:5]N1C(=O)CCC1=O)=O.[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:31])[CH2:29][OH:30])=[CH:24][CH:23]=1>C1COCC1>[OH:30][CH2:29][C@H:28]([NH:31][C:3](=[O:5])[C@@H:2]([CH3:1])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 90026070HCID 90026070、化合物

生成物 1

HCID 90025824HCID 90025824、化合物収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
48 °C

実験手順

To a solution consisting of (±)-2,5-dioxopyrrolidin-1-yl 2-methyl-5-phenyl pentanoate (18mb(i), 85.6 g, 296 mmol) in THF (3000 mL) at 48° C. was added R-(−)-2-phenylglycinol (65.9 g, 480 mmol, Bridge Organics) in portions. The resulting reaction mixture was stirred at 48° C. for 40 hours. A white precipitate formed, which was filtered from the reaction mixture and washed with THF. The filtrate was concentrated under vacuum and the residue, comprising the diastereomeric pair, was chromatographed on silica gel. Elution with ethyl acetate-heptane (50:50 v/v) afforded the pure diastereomer title compound (31.3 g, 34%) as a colorless solid; TLC Rf 0.205 (solvent system: 50:50 v/v ethyl acetate-heptane); HPLC retention time 15.1 minutes, stationary phase: Gemini 5μ C18 250×4.6 mm, ultraviolet detector at 210 nm, mobile phase: 1 mL/min, 60:40:0.1 v/v methanol-water-acetic acid.

後処理

  1. customThe resulting reaction mixture
  2. customA white precipitate formed
  3. filtrationwhich was filtered from the reaction mixture
  4. washwashed with THF
  5. concentrationThe filtrate was concentrated under vacuum
  6. customwas chromatographed on silica gel
  7. washElution with ethyl acetate-heptane (50:50 v/v)

出典と根拠

ORDレコード
ord-845b5e6a71054bcaa8d4933eb583801c
出典データセット
uspto-grants-2016_09
特許番号
US09440919B2

関連ノート

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