Cyclohexanone → benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

HRID 1034958노트

반응식

HRID 1034958 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9]2)[CH:3]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:9]2)[C:3]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

참가 물질

4

반응물 2

HCID 7967CyclohexanoneHCID 69162082benzyl 3-(5-amino-1-methyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylate

생성물 1

HCID 69162390benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate수율 53%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of EXAMPLE 24C (1.78 g, 5.92 mmol) and cyclohexanone (1.23 mL, 11.85 mmol) in acetic acid (10 mL) was stirred at ambient temperature overnight and at 55° C. for 1 day. The acetic acid was removed and the residue partitioned between sodium bicarbonate solution and ethyl acetate. The organic phase was washed with water, concentrated and the residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane to provide the title compound as a light yellow solid (1.19 g, 53%). MS (DCI): m/z 381 (M+H)+.

후처리

  1. customThe acetic acid was removed
  2. customthe residue partitioned between sodium bicarbonate solution and ethyl acetate
  3. washThe organic phase was washed with water
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography on silica gel using 70-90% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-524120b59ee94e51a667fd2808e326fb
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546368B2

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