Tetramethylammonium fluoride → 2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661547

反応式

HRID 661547 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][CH2:35][CH3:36])[C:13]([C:15]1[CH:16]=[C:17]2[CH:23]=[CH:22][N:21]([Si](C(C)C)(C(C)C)C(C)C)[C:18]2=[N:19][CH:20]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+](C)(C)C.[F-]>C1COCC1.C([O-])(O)=O.[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:34][CH2:35][CH3:36])[C:13]([C:15]1[CH:16]=[C:17]2[CH:23]=[CH:22][NH:21][C:18]2=[N:19][CH:20]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 2

HCID 67803Tetramethylammonium fluorideHCID 666874762-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 666883852-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester収率 86%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a stirred solution of 2-propyl-2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.415 g, 0.809 mmol) in THF (7.5 mL) at ambient temperature under nitrogen was added TMAF (0.753 g, 8.09 mmol). The reaction mixture was stirred for one hour, then diluted with saturated aqueous NaHCO3 (30 mL) and water (15 mL) and extracted with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to a pale yellow gum. Purification by chromatography (silica, 50 to 100% EtOAc in hexanes) gave 2-propyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.247 g, 0.692 mmol, 86%) as a colourless foam.

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a pale yellow gum
  6. customPurification by chromatography (silica, 50 to 100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-1b7af6127ab44d9eba0ecfe7a45452cc
出典データセット
uspto-grants-2011_12
特許番号
US08084623B2

関連ノート

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