Water → HCID 178461668, 화합물

HRID 922351

반응식

HRID 922351 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 7961BromobenzeneHCID 178418306HCID 178418306, 화합물HCID 178461670HCID 178461670, 화합물2회

생성물 1

HCID 178461668HCID 178461668, 화합물수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of bromobenzene (4.93 g, 31.4 mmol) in THF 125 mL under nitrogen at −78° 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)aziridin-2-yl)methanol EBE 06066 (3.13 g, 86% yield).

후처리

  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

출처 및 근거

ORD 기록
ord-94f8f0463788420ba1f9bb806f1b4b52
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278943B2

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