Triethylsilane → 2-(Trifluoromethyl)piperazine

HRID 992348노트

반응식

HRID 992348 반응식
[SiH](CC)(CC)CC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH:22]1[C:34]([F:37])([F:36])[F:35])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(C(F)(F)F)=O.CC(O)=O>[CH2:14]([N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:23][CH:22]1[C:34]([F:36])([F:37])[F:35])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[F:35][C:34]([F:37])([F:36])[CH:22]1[CH2:23][NH:24][CH2:25][CH2:26][NH:21]1

참가 물질

7

반응물 3

HCID 12052TriethylsilaneHCID 18519781Dibenzyl-2-trifluoromethylpiperazineHCID 21226445Aluminium lithium hydride

생성물 2

HCID 185197252-(Trifluoromethyl)piperazineHCID 18519781Dibenzyl-2-trifluoromethylpiperazine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6422Trifluoroacetic acid용매

실험 절차

2-Trifluoromethylpiperazine (Jenneskens et al., Ref. 31c) was prepared through a four step route (Scheme 6). Using Lewis acid TiCl4, N,N′-dibenzylethylenediamine 11 reacted with trifluoropyruvates 12 to afford hemiacetal 13, which was reduced at room temperature by Et3SiH in CF3COOH to lactam 14. LiAlH4 treatment then reduced lactam 14 to 1,4-dibenzyl-2-trifluoromethylpiperazine 15. Finally, hydrogenation of compound 15 in HOAc gave the desired product 2-trifluoromethylpiperazine 16.

출처 및 근거

ORD 기록
ord-8483921fe6a7400d934f0b45e7313323
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469006B1

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