1-Tert-butyl 4-ethyl 4-(2-cyanoethyl)piperidine-1,4-dicarboxylate → tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 41537노트

반응식

HRID 41537 반응식
[C:1]([CH2:3][CH2:4][C:5]1([C:18]([O:20]CC)=O)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:2]>N.[Ni]>[O:20]=[C:18]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:1][NH:2]1

참가 물질

4

반응물 1

HCID 672523241-Tert-butyl 4-ethyl 4-(2-cyanoethyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 49760149tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate수율 41%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 222Ammonia용매

실험 절차

A heterogeneous mixture of Raney Ni (5.0 g) in ethanolic ammonia (˜20% v/v) and 1-tert-butyl 4-ethyl 4-(2-cyanoethyl)piperidine-1,4-dicarboxylate (8.5 g, 27.42 mmol) was hydrogenated at 100 psi for 48 h at rt in an autoclave. After completion of the reaction, the catalyst was filtered off and washed with ethanol. The combined filtrate was concentrated under reduced pressure and triturated with n-pentane to yield a solid which was purified by column chromatography (eluent=6% methanol in chloroform) to furnish the title compound as a white solid (3.0 g, 41%). [1H-NMR (DMSO-d6, 300 MHz): δ 7.38 (s, 1H), 3.68-3.60 (m, 2H), 3.18-2.95 (m, 4H), 1.89-1.58 (m, 4H), 1.45-1.22 (m, 13H); HPLC RtA=3.835 min (96%); LCMS RtA=1.630, [M+H-Boc]+=169.1].

후처리

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. washwashed with ethanol
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. customtriturated with n-pentane
  6. customto yield a solid which
  7. customwas purified by column chromatography (eluent=6% methanol in chloroform)

출처 및 근거

ORD 기록
ord-386befaaf23f40a9bde49017cdee46b4
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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