4-tert-Butylphenyl glycidyl ether, (+)- → (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 237730노트

반응식

HRID 237730 반응식
[N:1]#[C:2][NH2:3].[Na].[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@@H:15]2[CH2:17][O:16]2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([C:9]1[CH:19]=[CH:18][C:12]([O:13][CH2:14][C@H:15]2[O:16][C:2]([NH2:3])=[N:1][CH2:17]2)=[CH:11][CH:10]=1)([CH3:6])([CH3:7])[CH3:8]

참가 물질

4

반응물 2

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 57375518Cyanamidnatrium

생성물 1

HCID 67060987(S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine수율 41%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a vigorously stirred solution of sodium hydrogen cyanamide (2.92 g, 44.5 mmol) in methanol (40 mL) was added dropwise (S)-2-(4-tert-butylphenoxymethyl)-oxirane (9.18 g, 44.5 mmol). The reaction mixture was stirred at room temperature overnight after which the reaction mixture was concentrated to remove methanol. Anhydrous diethyl ether (150 mL) was added. The resulting white precipitate was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride) to give 4.53 g (41%) of (S)-5-(4-tert-butyl-phenoxymethyl)-(4,5-dihydro-oxazol-2-yl)amine.

후처리

  1. concentrationwas concentrated
  2. customto remove methanol
  3. additionAnhydrous diethyl ether (150 mL) was added
  4. filtrationThe resulting white precipitate was filtered through celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography (silica, 7N NH3 in methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-626b2a8eccaf447a9d00c52e8afc40d5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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