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

HRID 1642482노트

반응식

HRID 1642482 반응식
[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

참가 물질

5

반응물 3

HCID 22635083Tetrahydrofuran tolueneHCID 57619828Ethyl 3-cyano-3-(4-hydroxypiperidin-1-YL)pyrrolidine-1-carboxylateHCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9bd80f7fd2b14061af3d19f04db1766f
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119661B2

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