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

HRID 712970

反応式

HRID 712970 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9c154f7b8f3a4db8bdc45ae2bfcdf926
出典データセット
uspto-grants-2015_11
特許番号
US09181273B2

関連ノート

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