Hydrochloric Acid → 1-(alpha-methylbenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

HRID 323441노트

반응식

HRID 323441 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[CH2:11]([O:13][CH2:14][CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][C:34]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:38][CH2:37][NH:36][CH2:35]2)[CH2:28][CH2:27]1)[CH3:12].C([BH3-])#N.[Na+].Cl>CO.BrCOC1C(O)=CC=C(C)C=1.C(OCC)(=O)C>[CH3:2][CH:1]([N:36]1[CH2:37][CH2:38][C:34]([CH2:33][CH2:32][N:29]2[CH2:30][CH2:31][CH:26]([NH:25][C:17]3[N:16]([CH2:15][CH2:14][O:13][CH2:11][CH3:12])[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=3)[CH2:27][CH2:28]2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:35]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 5003444Sodium cyanoborohydrideHCID 220090993-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt

생성물 1

HCID 178956821-(alpha-methylbenzyl)-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine

시약·촉매·용매 3

HCID 86612474Bromocreosol촉매HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매

실험 절차

According to the method of J. Am. Chem. Soc., 93, 2897 (1971), combine acetophenone (10 mmol) and 3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine hydrochloric acid salt (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (10 mmol) in methanol (100 mL). Add bromocreosol green (0.5% by weight in methanol, 1 drop). Add dropwise, a solution of sodium cyanoborohydride (10 mL, 1M in tetrahydrofuran, 10 mmol) and at the same time maintain the pH of the reaction mixture, as indicated by a yellow color for the indicator, by the addition of a 5 M solution of hydrochloric acid in methanol. When the reaction is complete, concentrate the reaction mixture in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

후처리

  1. additionAdd dropwise
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto obtain a residue
  4. extractionextract with water
  5. customSeparate the layers
  6. dry with materialdry the organic layer over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-394e22d4ba0b463b95ef6450faf46722
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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