3,5-Bis(trifluoromethyl)benzaldehyde → HCID 86648399、化合物

HRID 409461ノート

反応式

HRID 409461 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]([F:31])([F:30])[C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH:21]=O.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:21][C:20]2[CH:23]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:25]=[C:18]([C:17]([F:16])([F:30])[F:31])[CH:19]=2)[CH2:10][C@H:9]1[CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 59614425HCID 59614425、化合物

生成物 1

HCID 86648399HCID 86648399、化合物収率 81.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (2R,4S)-4-amino-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (150 mg, 0.7 mmol) in methanol (2 mL) is added to 3,5-bis-trifluoromethyl-benzaldehyde (340 mg, 1.4 mmol), and the reaction mixture is stirred at room temperature. After stirring for overnight, sodium borohydride (53 mg, 1.4 mmol) is added. After stirring for additional 1 hour, The product is extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give crude (2R,4S)-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (250 mg).

後処理

  1. stirringAfter stirring for overnight
  2. stirringAfter stirring for additional 1 hour
  3. extractionThe product is extracted three times with EtOAc
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-af3fd20455734c2aa6219a5e92a54305
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

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