Sodium Hydroxide → HCID 57525626, 화합물

HRID 1594398노트

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HRID 1594398 반응식
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[CH3:10][O:11][C:12]1([O:21][CH3:22])[CH2:15][CH:14]([C:16](=O)[CH2:17][C:18]#[N:19])[CH2:13]1>CCO>[C:2]([N:6]1[C:18]([NH2:19])=[CH:17][C:16]([CH:14]2[CH2:15][C:12]([O:11][CH3:10])([O:21][CH3:22])[CH2:13]2)=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 81889tert-Butylhydrazine monohydrochlorideHCID 575256253-(3,3-Dimethoxy-cyclobutyl)-3-oxo-propionitrile

생성물 1

HCID 57525626HCID 57525626, 화합물수율 86%

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
75 °C

실험 절차

To a slurry of tert-butylhydrazine hydrochloride (45.1 g, 362.0 mmol) in EtOH (1 L) was added NaOH pellets (12.4 g, 310.3 mmol). After 30 min, crude 3-(3,3-dimethoxy-cyclobutyl)-3-oxo-propionitrile in EtOH (300 mL) was added. The resulting slurry was heated to 75° C. (oil bath). After 14 hr, the reaction was cooled to room temperature, filtered, and concentrated under reduced pressure. Isopropyl ether was added to the resulting slurry. The slurry was stirred for 15 min, filtered, and concentrated to yield a viscous oil. Trituration with ether/hexanes (several crops) gave the title compound (56.2 g, 86% yield over two steps) as a colorless solid: mp 80.9° C. 500 MHz 1H NMR (CDCl3) d 5.50 (s, 1H), 3.51 (bs, 2H), 3.18 (s, 3H), 3.16 (s, 3H), 3.19-3.14 (m, 1H), 2.60-2.54 (m, 2H), 2.20-2.14 (m, 2H), 1.59 (s, 9H). LRMS m/z (APCI+) 254 (M+1).

후처리

  1. waitAfter 14 hr
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionIsopropyl ether was added to the resulting slurry
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a viscous oil

출처 및 근거

ORD 기록
ord-8fe61927dc7642568b2a8ae8f5eba017
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07300944B2

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