Triethylsilane → 2-(Trifluoromethyl)piperazine

HRID 992348ノート

反応式

HRID 992348 の反応式
[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

参加物

7

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-8483921fe6a7400d934f0b45e7313323
出典データセット
uspto-grants-2002_10
特許番号
US06469006B1

反応ノート

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