3-Oxocyclobutane-1-carboxylic acid → 3-(3-Chloro-4-((pyrrolidin-1-yl)methyl)phenyl)-3-hydroxycyclobutanecarboxylic acid

HRID 1694414노트

반응식

HRID 1694414 반응식
[Li]CCCC.Br[C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:9]([Cl:19])[CH:8]=1.[O:20]=[C:21]1[CH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22]1>C1COCC1>[Cl:19][C:9]1[CH:8]=[C:7]([C:21]2([OH:20])[CH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22]2)[CH:18]=[CH:17][C:10]=1[CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

5

반응물 3

HCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 489354141-(4-Bromo-2-chlorobenzyl)pyrrolidineHCID 178418339Butyllithium

생성물 1

HCID 574858713-(3-Chloro-4-((pyrrolidin-1-yl)methyl)phenyl)-3-hydroxycyclobutanecarboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A 2.5 M solution of n-BuLi in hexanes (101 mL, 254 mmol) was added over 15 min to a solution of 1-(4-bromo-2-chlorobenzyl)pyrrolidine (69.6 g, 254 mmol) in absolute THF (450 ml) under a flow of nitrogen at −78° C. The reaction mixture was stirred at −78° C. for 30 min. Then a −78° C. chilled solution of 3-oxocyclobutanecarboxylic acid (14.4 g, 126.7 mmol) in absolute THF (150 ml) was added drop wise for 10 min at −78° C. The mixture was warmed to RT slowly and left stirring for 18 hrs and the resulting solution was used. LRMS m/z Calcd for C18H20NClO3, 309.8, found, 308.1 (M−H) APCI.

후처리

  1. additionwas added drop wise for 10 min at −78° C
  2. temperatureThe mixture was warmed to RT slowly
  3. waitleft
  4. stirringstirring for 18 hrs

출처 및 근거

ORD 기록
ord-340ec6bb7546446aa8b829af9ff30ab0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158673B2

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