Pyridine → 3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidine-1-carboxylic Acid Benzyl Ester

HRID 20922

반응식

HRID 20922 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([CH2:16][OH:17])[CH:13]([OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]N=1)C.[C:28](Cl)(C1C=CC=CC=1)([C:37]1[CH:44]=[CH:43][C:40]([O:41][CH3:42])=[CH:39][CH:38]=1)[C:29]1[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[CH:31][CH:30]=1.N1C=CC=C[CH:53]=1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([OH:18])[CH:14]([CH:16]([C:24]2[CH:53]=[CH:22][CH:27]=[CH:26][CH:25]=2)[O:17][CH:28]([C:29]2[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[CH:31][CH:30]=2)[C:37]2[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[CH:43][CH:44]=2)[CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 4

HCID 1049Pyridine2회HCID 218852-DimethylaminopyridineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 230620493-Hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic Acid Benzyl Ester

생성물 1

HCID 1317282233-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidine-1-carboxylic Acid Benzyl Ester

실험 절차

Referring to scheme 18, compound 74 (4.39 g, 17.5 mmol) was co-evaporated with anhydrous pyridine three times and then dissolved in pyridine (30 mL). To this solution dimethylamino pyridine (0.213 g, 1.75 mmol) and DMT-Cl (6.22 g, 18.4 mmol, 1.05 equiv.) were added at room temperature. The reaction mixture was stirred at room temperature for 16 h. The excess DMT-Cl was quenched by the addition of methanol (10 mL). The solution was dried under reduced pressure. To the residue was suspended in ethyl acetate (300 mL) and washed with saturated bicarbonate solution, brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was obtained after removal of the solvent. Upon purification over silica gel using 3% MeOH/DCM compound 75 (8.46 g, 87%) was obtained as white foamy solid.

후처리

  1. customThe excess DMT-Cl was quenched by the addition of methanol (10 mL)
  2. customThe solution was dried under reduced pressure
  3. washwashed with saturated bicarbonate solution, brine and water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-32593fb04bdc44d59d30b88895bd07e6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745608B2

연결된 노트

불러오는 중…