Acetic Acid → 1,1-Dimethylethyl 4-cyano[1,4′-bipiperidine]-1′-carboxylate

HRID 599726ノート

反応式

HRID 599726 の反応式
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.[C:29]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)#[N:30].CC(O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.O>[C:29]([CH:31]1[CH2:36][CH2:35][N:34]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:33][CH2:32]1)#[N:30]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 311Citric AcidHCID 1382234-CyanopiperidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 672736071,1-Dimethylethyl 4-cyano[1,4′-bipiperidine]-1′-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

6.09 g (27.3 mmol) of NaBH(OAc)3 were added batchwise to a suspension, cooled to 0° C., of 5.44 g (27.3 mmol) tert.butyl 4-oxo-piperidin-1-carboxylate, 3.00 g (27.2 mmol) 4-cyanopiperidine and 1.6 mL (28.0 mmol) AcOH in 400 mL DCM and the reaction mixture was stirred overnight, while warming up to RT. 400 mL water were added and the mixture was acidified with citric acid. The organic phase was separated off, the aqueous phase was made alkaline with saturated NaHCO3 solution and extracted exhaustively with DCM. The combined organic phases were concentrated by evaporation i. vac. and the residue was crystallised with a little DIPE.

後処理

  1. customThe organic phase was separated off
  2. extractionextracted exhaustively with DCM
  3. concentrationThe combined organic phases were concentrated by evaporation i
  4. customand the residue was crystallised with a little DIPE

出典と根拠

ORDレコード
ord-84f7c43108e947898e53d3f69177bf27
出典データセット
uspto-grants-2011_03
特許番号
US07897603B2

反応ノート

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