Hydrochloric Acid → (R)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

HRID 1601449ノート

反応式

HRID 1601449 の反応式
[C:1]1([C:7]2([C:28]([OH:30])=[O:29])[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C@:15]3([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=4)[CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48])[C:41](Cl)=[O:42].Cl>O1CCCC1.O>[CH3:50][O:49][C:45]1[CH:44]=[C:40]([CH:39]=[C:38]([O:37][CH3:36])[C:46]=1[O:47][CH3:48])[C:41]([N:17]1[CH2:18][CH2:19][C@:15]([CH2:14][CH2:13][N:10]2[CH2:11][CH2:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:28]([OH:30])=[O:29])[CH2:8][CH2:9]2)([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:16]1)=[O:42]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 53783991(S)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

生成物 1

HCID 53652197(R)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Combine (S)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (50 g, 112 mmol) and sodium bicarbonate (30 g) in tetrahydrofuran (1300 mL) and water (300 mL). Add portionwise over about 45 minutes, a solution of 3,4,5-trimethoxybenzoyl chloride (26 g, 112 mmol) in tetrahydrofuran (130 mL). After 2 hours, dilute with water (1000 mL). Adjust the pH to about 4 using concentrated aqueous hydrochloric acid to give a solid. Collect the solid by filtration and rinse with water. Triturate the solid with methanol (1300 mL) and water (1300 mL). Filter, rinse with water and dry in vacuo to give the title compound.

後処理

  1. additionAdd portionwise over about 45 minutes
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with water
  6. customTriturate the solid with methanol (1300 mL) and water (1300 mL)
  7. filtrationFilter
  8. washrinse with water
  9. customdry in vacuo

出典と根拠

ORDレコード
ord-20ce7c95e6a04f91ba682995298b5855
出典データセット
uspto-grants-1999_11
特許番号
US05977139

反応ノート

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