Tetrahydrofuran toluene → Ethyl 3-(4-hydroxypiperidin-1-YL)-3-methylpyrrolidine-1-carboxylate

HRID 1642482ノート

反応式

HRID 1642482 の反応式
[C:1]([C:3]1([N:13]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1)#N.C[Mg]Br.C1(C)C=CC=CC=1.C1COCC1>O1CCCC1>[OH:19][CH:16]1[CH2:17][CH2:18][N:13]([C:3]2([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]2)[CH2:14][CH2:15]1

参加物

5

反応物 3

HCID 22635083Tetrahydrofuran tolueneHCID 57619828Ethyl 3-cyano-3-(4-hydroxypiperidin-1-YL)pyrrolidine-1-carboxylateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 57619796Ethyl 3-(4-hydroxypiperidin-1-YL)-3-methylpyrrolidine-1-carboxylate収率 86.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of ethyl 3-cyano-3-(4-hydroxy-1-piperidyl)pyrrolidine-1-carboxylate (1.0 gm, 3.74 mmol) in tetrahydrofuran (25 mL) was added a 1.4 M solution of methyl magnesium bromide in toluene/THF (5.35 mL, 7.48 mmol) at 0° C., and the mixture was allowed to warm to room temperature. The mixture was stirred for another 12 h at room temperature, the reaction was quenched with saturated ammonium chloride solution (5 mL) at 0° C. and diluted with ethyl acetate (25 mL). The layers were separated and the organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound as a pale solid (830 mg), which was used for the subsequent step without further purification. MS (M+1): 257.16.

後処理

  1. customthe reaction was quenched with saturated ammonium chloride solution (5 mL) at 0° C.
  2. additiondiluted with ethyl acetate (25 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9bd80f7fd2b14061af3d19f04db1766f
出典データセット
uspto-grants-2012_02
特許番号
US08119661B2

反応ノート

読み込み中…