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(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide → (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide

HRID 412636
ノート
印刷プレビュー

反応式

HRID 412636 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][N:21](CC2C=CC=CC=2)[CH2:20]1)=[O:17]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:11]([NH:10][CH2:15][CH3:14])[CH3:12].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 57172017(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide

生成物 2

HCID 8021DiethylamineHCID 57279632(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide収率 4.1%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

20% w/w Palladium hydroxide on carbon (12.5 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide (62.5 mg) [see Example 1] in ethanol (10 ml). The reaction mixture was hydrogenated at 414 kPa (60 p.s.i.) for 56 hours, after which time the catalyst was filtered off and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate:diethylamine to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide (1 mg) as an oil.

後処理

  1. filtrationafter which time the catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate

出典と根拠

ORDレコード
ord-8d8333426cc843e784b9fed7037fdbf9
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06562964B1

反応ノート

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