Cesium carbonate → (S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

HRID 390305ノート

反応式

HRID 390305 の反応式
C1(C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1P(C(C)(C)C)C(C)(C)C.Br[C:31]1[N:36]=[C:35]([O:37][CH3:38])[C:34]([N+:39]([O-:41])=[O:40])=[CH:33][CH:32]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:48]([O:52][C:53]([N:55]1[CH2:59][CH2:58][CH2:57][C@H:56]1[CH2:60][OH:61])=[O:54])([CH3:51])([CH3:50])[CH3:49]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:48]([O:52][C:53]([N:55]1[CH2:59][CH2:58][CH2:57][C@H:56]1[CH2:60][O:61][C:31]1[CH:32]=[CH:33][C:34]([N+:39]([O-:41])=[O:40])=[C:35]([O:37][CH3:38])[N:36]=1)=[O:54])([CH3:51])([CH3:50])[CH3:49]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 643448(S)-(-)-N-Boc-prolinolHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 122692236-Bromo-2-methoxy-3-nitropyridine

生成物 1

HCID 66883424(S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester収率 7.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

To a mixture of Pd(OAc)2 (0.08 g, 0.34 mmol) and [1,1′]binaphthalen-2-yl-di-tert-butyl-phosphane (0.14 g, 0.34 mmol) in toluene (10 ml) was added 6-bromo-2-methoxy-3-nitropyridine(1.0 g, 4.29 mmol), Cs2CO3 (3.5 g, 10.73 mmol), and (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.73 g, 8.58 mmol). The mixture was stirred under nitrogen at room temperature for 24 h. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent to provide 0.11 g (7.5%) of the product.

後処理

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent

出典と根拠

ORDレコード
ord-daa5133780a24e8ea1a1896e1fb710be
出典データセット
uspto-grants-2013_02
特許番号
US08383641B2

反応ノート

読み込み中…