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

HRID 390305노트

반응식

HRID 390305 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-daa5133780a24e8ea1a1896e1fb710be
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383641B2

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