1,2-Dichloroethane → tert-butyl 2,4-dioxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridine-1-carboxylate

HRID 885902

反応式

HRID 885902 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH3:21][C:22]1(C)OC(=O)CC(=O)[O:23]1.OS([O-])(=O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[O:23]=[C:22]1[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14](=[O:16])[CH2:21]1

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516919Sodium BisulfateHCID 35647322-((tert-Butoxycarbonyl)amino)cyclopentanecarboxylic acid

生成物 1

HCID 86642118tert-butyl 2,4-dioxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridine-1-carboxylate収率 93.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (0.24 g, 1.06 mmol) in DCM (4.5 mL) was added EDC (0.31 g, 1.59 mmol), DMAP (0.19 g, 1.59 mmol) and Meldrum's acid (0.15 g, 1.06 mmol). After stirring for 18 h at r.t., the reaction mixture was poured into aqueous 1M NaHSO4 solution (5 mL) and extracted with DCM (3×20 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to give a clear yellow oil which was dissolved in EtOAc (5 mL) and heated to 80° C. for 18 h. The reaction mixture was then cooled and concentrated in vacuo to give the title compound (0.25 g, 42%) as a yellow solid that was used without further purification. δH (CDCl3) 4.64-4.55 (1H, m), 2.98-2.92 (1H, m), 2.37-2.20 (2H, m), 1.99-1.60 (6H, m), 1.58 (9H, s). LCMS (ES+) 198.0 ((M−tBu)+H)+.

後処理

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a clear yellow oil which
  6. temperatureheated to 80° C. for 18 h
  7. temperatureThe reaction mixture was then cooled
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c5e322381b244f1188d9e42a010d8aaf
出典データセット
uspto-grants-2012_08
特許番号
US08242116B2

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