Hydrochloric Acid → (R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amine dihydrochloride

HRID 1622180ノート

反応式

HRID 1622180 の反応式
C(C1C=CC(N2CC[C@H](N[C@@H](C3C4C(=CC=CC=4)C=CC=3)C)C2)=CC=1)(=O)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C@H:36]([NH:38][C@H:39]2[CH2:43][CH2:42][N:41]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=3)[CH2:40]2)[CH3:37])[CH:33]=[CH:34][CH:35]=1.[ClH:55]>C(OCC)(=O)C>[ClH:55].[ClH:55].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C@H:36]([NH:38][C@H:39]2[CH2:43][CH2:42][N:41]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:53])([F:54])[F:52])[CH:46]=3)[CH2:40]2)[CH3:37])[CH:33]=[CH:34][CH:35]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 58973474(R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amineHCID 58973483(S)-1-(4-acetylphenyl)pyrrolidin-3-yl-[(R)-1-(naphthalen-1-yl)ethyl]amine

生成物 1

HCID 67410838(R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amine dihydrochloride

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a suspension of 176 mg of (S)-3-[(R)-1-(3-methoxyphenyl)ethylamino]pyrrolidine dihydrochloride, 110 mg of (3-trifluoromethyl)benzaldehyde and 636 mg of sodium triacetoxyborohydride in 10 ml of methylene chloride was added several drops of acetic acid, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried, the solvent was removed, and then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 91.2 mg of (R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amine. (2) In 10 ml of ethyl acetate was dissolved 91.2 mg of (R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amine, and 1 ml of a solution of 4M hydrochloric acid in ethyl acetate was added, and the mixture was stirred. The reaction mixture was evaporated, diethyl ether was added to the residue, and after collecting the precipitates by filtration, it was washed with diethyl ether and dried to obtain 70.4 mg of (R)-1-(3-methoxyphenyl)ethyl-[(S)-1-(3-trifluoromethylbenzyl)pyrrolidin-3-yl]amine dihydrochloride (Example 4.001 in the following Table B).

後処理

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. additiondiethyl ether was added to the residue
  4. customafter collecting the
  5. customprecipitates by filtration, it
  6. washwas washed with diethyl ether
  7. customdried

出典と根拠

ORDレコード
ord-12254b42ec8147cdb34062e2504ad531
出典データセット
uspto-grants-2014_07
特許番号
US08778628B2

反応ノート

読み込み中…