Triethylamine → 4-tert-butoxycarbonyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 1363301

反応式

HRID 1363301 の反応式
[O:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O.CCOC(C)=O.CCCCCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:12][O:11][C:9]([C:6]1[N:5]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[C:4]2[CH:3]=[CH:2][O:1][C:8]=2[CH:7]=1)=[O:10]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 596486034-tert-butoxycarbonyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester収率 62%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (1.0 g, 6.06 mmol) in CH2Cl2 (10 ml) was added triethyl amine (1.85 g, 18.2 mmol) and DMAP (148 mg 1.22 mol). Then BOC2O (2.0 g, 9.1 mmol) was added. The resulting mixture was stirred overnight. After the reaction was complete as judged TLC analysis (10% EtOAc/hexane), the reaction mixture was washed with water and brine and dried over Na2SO4. After filtration, the filtrate was concentrated and the crude product was purified by silica gel chromatography (20% EtOAc in hexane) to give 4-tert-butoxycarbonyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester as a white solid (987 mg, 62%). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.45 (d, J=1.47 Hz, 1H), 6.82 (s, 1H), 6.59 (s, 1H), 3.80 (s, 3H), 1.55 (s, 9H).

後処理

  1. washthe reaction mixture was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated
  5. customthe crude product was purified by silica gel chromatography (20% EtOAc in hexane)

出典と根拠

ORDレコード
ord-19c654556d1c4c8e9feb0d3ef25eceef
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

関連ノート

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