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

HRID 1770974

反応式

HRID 1770974 の反応式
[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]

参加物

7

反応物 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 679796166'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-one2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8857Ethyl Acetate溶媒HCID 178479889HCID 178479889、化合物溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-946b4d24b76842dcb3297b92e0afdeaf
出典データセット
uspto-grants-2016_02
特許番号
US09248129B2

関連ノート

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