Water → N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 1770974

반응식

HRID 1770974 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:14][CH2:13][CH2:12]3)[C:8]2=O)=[CH:4][CH:3]=1.[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O.CCOC(C)=O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]1([CH2:14][CH2:13][CH2:12]1)[C:8]2=[N:21][S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20]

참가 물질

7

반응물 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 679796166'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-one2회

생성물 1

HCID 67979440N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide수율 135.3%

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8857Ethyl Acetate용매HCID 178479889HCID 178479889, 화합물용매

실험 절차

6′-Bromospiro[cyclobutane-1,2′-inden]-1′(3′H)-one (Intermediate 38, 1.1 g, 4.38 mmol), 2-methylpropane-2-sulfinamide (0.96 g, 7.88 mmol), and titanium ethoxide (1.805 mL, 8.76 mmol) were dissolved in methyl THF (20 mL), and heated to reflux overnight. The reaction was allowed to cool to r.t., then it was diluted with EtOAc (150 mL). Water (22 mL) was added dropwise over 10 min under vigorous stirring and then the mixture was left standing without stirring for 1.5 h. The solids were filtered off and the organics were evaporated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetate 8:1) to afford the title compound (2.1 g, 77% yield), used as such in the next step: MS (ES+) m/z 354 [M+H]+.

후처리

  1. temperatureheated
  2. temperatureto reflux overnight
  3. waitthe mixture was left
  4. stirringwithout stirring for 1.5 h
  5. filtrationThe solids were filtered off
  6. customthe organics were evaporated
  7. customto give a crude product which
  8. customwas purified by flash chromatography (eluent: heptane/ethylacetate 8:1)

출처 및 근거

ORD 기록
ord-946b4d24b76842dcb3297b92e0afdeaf
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248129B2

연결된 노트

불러오는 중…