3,5-Bis(trifluoromethyl)benzaldehyde → HCID 86648399, 화합물

HRID 409461노트

반응식

HRID 409461 반응식
[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]

참가 물질

5

반응물 3

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 59614425HCID 59614425, 화합물

생성물 1

HCID 86648399HCID 86648399, 화합물수율 81.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-af3fd20455734c2aa6219a5e92a54305
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759365B2

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