Water → HCID 178461668、化合物

HRID 906652

反応式

HRID 906652 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]C(C)(C)C.[C:13]1([C@@H:19]([N@:21]2[CH2:23][CH:22]2[CH:24]=[O:25])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1COCC1>[C:2]1([C@H:24]([CH:22]2[CH2:23][N@@:21]2[C@H:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:20])[OH:25])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 7961BromobenzeneHCID 178418306HCID 178418306、化合物HCID 178461670HCID 178461670、化合物2 回

生成物 1

HCID 178461668HCID 178461668、化合物収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of bromobenzene (4.93 g, 31.4 mmol) in THF 125 mL under nitrogen at −78° C. was added t-BuLi (1.7 M in pentane, 50 mL). The mixture was stirred for 0.5 h at room temperature. The mixture was cooled down to −78° C. and a solution of (R)-1-((S)-1-phenylethyl)aziridine-2-carbaldehyde EBE 06048 (2.5 g, 14.3 mmol) in THF (16.7 mL) at −78° C. was added dropwise. The reaction mixture was treated with H2O (20 mL), the organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a residue that was purified by column chromatography using a gradient of 0-20% [v/v] EtOAc in cyclohexane to give (R)-phenyl((R)-1-((S)-1-phenylethyl)aziridine-2-yl)methanol EBE 06066 (3.13 g, 86% yield).

後処理

  1. temperatureThe mixture was cooled down to −78° C.
  2. customthe organic layer was separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue that
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-9ce6d280e4ff4cdd9cb59ef50d3fc394
出典データセット
uspto-grants-2011_09
特許番号
US08013000B2

関連ノート

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