Acetic Acid → (2S,5R)-1-benzyl-2,5-dimethyl-4-(3,3,3-trifluoropropyl)piperazine

HRID 331072

반응식

HRID 331072 반응식
[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[NH:11][CH2:10][C@@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:22])([F:21])[CH2:18][CH:19]=O.CC(O)=O.C([BH3-])#N.[Na+]>C1COCC1.CO>[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11]([CH2:19][CH2:18][C:17]([F:22])([F:21])[F:16])[CH2:10][C@@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5003444Sodium cyanoborohydrideHCID 23402345(2S,5R)-1-Benzyl-2,5-dimethylpiperazine

생성물 1

HCID 57519197(2S,5R)-1-benzyl-2,5-dimethyl-4-(3,3,3-trifluoropropyl)piperazine수율 92.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2S,5R)-1-benzyl-2,5-dimethylpiperazine (2.00 g, 7.21 mmol) in THF (10 mL), MeOH (10 mL), and TEA (1.0 mL) was added 3,3,3-trifluoropropionaldehyde (1.62 g, 14.4 mmol) and AcOH (0.826 mL, 14.4 mmol) followed by sodium cyanoborohydride (0.907 g, 14.4 mmol). The reaction was allowed to stir for 2 h, at which time the reaction was quenched with water (15 mL) then made basic with NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated in vacuo to yield a white powder (2.0 g, 90%). Mass Spectrum: Calcd for C16H24N2F3 (M+H): 301. Found: 301.

후처리

  1. customwas quenched with water (15 mL)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5fb63c3cc11c4bfaa5073acd941316eb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877761B2

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