Sodium Hydroxide → (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-ethylcyclopent-2-ene-1-carboxylic acid

HRID 1844305ノート

反応式

HRID 1844305 の反応式
[CH3:1][C:2]1[N:3]([C@H:8]2[CH2:12][C@@:11]([CH2:17][CH3:18])([C:13]([O:15]C)=[O:14])[CH:10]=[CH:9]2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-].[Na+]>CO>[CH3:7][C:4]1[N:3]([C@H:8]2[CH2:12][C@@:11]([CH2:17][CH3:18])([C:13]([OH:15])=[O:14])[CH:10]=[CH:9]2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 58305845methyl(1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-ethylcyclopent-2-ene-1-carboxylate

生成物 1

HCID 58305864(1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-ethylcyclopent-2-ene-1-carboxylic acid収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-ethylcyclopent-2-ene-1-carboxylate (12.94 g, 52.3 mmol) in methanol (100 ml) was treated with 2.5 N NaOH (30 ml, 75.0 mmol) and stirred at room temperature. After 15 hours more 2.5 N NaOH (10 ml, 25.0 mmol) was added and the reaction was stirred for an additional four days. The methanol was removed under reduced pressure and the residue partitioned between diethyl ether and water. The layers were separated and the aqueous was acidified with 4 N HCl, extracted twice with ethyl acetate, washed with brine, dried over MgSO4, and concentrated under reduced pressure to give (1R,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-ethylcyclopent-2-ene-1 carboxylic acid as a brown oil (11.83 g, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 5.98-5.96 (2H), 5.73 (2H), 5.30-5.26 (1H), 2.47-2.35 (2H), 2.20 (6H), 1.82-1.77 (2H), 0.96-0.92 (3H).

後処理

  1. stirringthe reaction was stirred for an additional four days
  2. customThe methanol was removed under reduced pressure
  3. customthe residue partitioned between diethyl ether and water
  4. customThe layers were separated
  5. extractionextracted twice with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e78094dcbf804464a1a4cdaa07f1f2ec
出典データセット
uspto-grants-2015_02
特許番号
US08946413B2

反応ノート

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