Diisopropylethylamine → Tert-butyl 4-[[benzyl-[2-oxo-2-(2-pyridyl)ethyl]amino]methyl]-4-hydroxy-piperidine-1-carboxylate

HRID 72885

반응식

HRID 72885 반응식
[CH2:1]([NH:8][CH2:9][C:10]1([OH:23])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br.Br[CH2:35][C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)=[O:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:9][C:10]1([OH:23])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11]1)[CH2:35][C:36](=[O:37])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromideHCID 68291338Tert-butyl 4-((benzylamino)methyl)-4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 68291423Tert-butyl 4-[[benzyl-[2-oxo-2-(2-pyridyl)ethyl]amino]methyl]-4-hydroxy-piperidine-1-carboxylate수율 92%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To tert-butyl 4-[(benzylamino)methyl]-4-hydroxy-piperidine-1-carboxylate (3.0 g, 9.36 mmol) in DMF (19 mL) at 0° C. was added diisopropyl ethylamine (3.4 mL, 19.66 mmol) followed by the addition of 2-bromo-1-(2-pyridyl)ethanone hydrobromide salt (2.6 g, 9.36 mmol) and reaction mixture was stirred for 2 hours warming from 0° C. to 10° C. The reaction mixture was diluted with ethyl acetate and washed with sat. NaHCO3 solution and then brine. The organics were separated, dried over Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified using silica gel column chromatography using MeOH/DCM (1-15%) as eluent to give tert-butyl 4-[[benzyl-[2-oxo-2-(2-pyridyl)ethyl]amino]methyl]-4-hydroxy-piperidine-1-carboxylate (3.8, 92%). ESI-MS m/z calc. 439.2. Found 440.0 (M+1)+; Retention time: 1.12 minutes (3 min run).

후처리

  1. temperaturewarming from 0° C. to 10° C
  2. washwashed with sat. NaHCO3 solution
  3. customThe organics were separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue, which
  8. customwas purified

출처 및 근거

ORD 기록
ord-95922c8713b64476bfe983225eb4b428
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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