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Cesium carbonate → 1-tert-Butyl 2-methyl (2S,4R)-4-[(3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 2045723
ノート
印刷プレビュー

反応式

HRID 2045723 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:17][C@@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)(=O)=O)=CC=1.[CH2:34]([CH:37]1[CH:46](O)[C:45]23[N:48]=[CH:49][CH:50]=[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]3[N:39]([CH3:51])[CH2:38]1)[CH:35]=[CH2:36]>CN1C(=O)CCC1.CCOC(C)=O.Cl>[CH2:34]([CH:37]1[CH:46]([O:17][C@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)[C:45]23[N:48]=[CH:49][CH:50]=[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]3[N:39]([CH3:51])[CH2:38]1)[CH:35]=[CH2:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 668963203-Allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-ol

生成物 1

HCID 866495141-tert-Butyl 2-methyl (2S,4R)-4-[(3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate収率 44%

試薬・触媒・溶媒 3

HCID 313
Hydrochloric Acid
溶媒
HCID 8857Ethyl Acetate溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
60 °C

実験手順

Cs2CO3 (8.20 g, 25.20 mmol) and 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (3.80 g, 8.18 mmol) were added in sequence to a solution of 3-allyl-1-methyl-3H-pyrrolo[2,3-e]quinolin-4-ol (1.50 g, 6.29 mmol) in NMP (42 mL). The mixture was heated at 60° C. for 12 h, then cooled and diluted with EtOAc and aqueous HCl (1 N). The organic layer was separated, washed with brine and dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was purified on silica gel (gradient elution, 20-100% EtOAc/petrol ether) to afford the title compound (1.30 g, 44%) as a solid. LCMS (ES+) m/z 466 (M+H)+.

後処理

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and removal of the volatiles
  6. customgave a residue that
  7. customwas purified on silica gel (gradient elution, 20-100% EtOAc/petrol ether)

出典と根拠

ORDレコード
ord-978cf036560348e8863acaf23c490a67
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08591878B2

反応ノート

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