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

HRID 599726노트

반응식

HRID 599726 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84f7c43108e947898e53d3f69177bf27
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897603B2

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