3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester → (3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 1945496ノート

反応式

HRID 1945496 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C:10]([CH3:20])([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH3:20][C:10]1([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:11][CH2:12][NH:8][CH2:9]1

参加物

5

反応物 1

HCID 596056303-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 63140531(3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanone収率 79.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 3-methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (330 mg, 1.17 mmol) in TFA (5 mL), DCM (5 mL) and water (0.1 mL) was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was taken up in MeOH and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH and the desired product was eluted with 2M NH3 in MeOH. The solvents were removed to give (3-Methylpyrrolidin-3-yl)pyrrolidin-1-ylmethanone as a white solid (169 mg, 79%). 1H NMR (400 MHz, CHCl3-d): δ 3.55-3.40 (m, 5 H); 3.06-2.92 (m, 2 H); 2.32-2.20 (m, 2 H); 2.01-1.82 (m, 5 H); 1.71 (m, 1 H); 1.33 (s, 3 H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. washThe cartridge was washed with MeOH
  3. washthe desired product was eluted with 2M NH3 in MeOH
  4. customThe solvents were removed

出典と根拠

ORDレコード
ord-5afd057523c6456fbe594783550aed88
出典データセット
uspto-grants-2013_03
特許番号
US08394796B2

反応ノート

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