Methyl benzilate → (1-Methylpiperidin-4-yl)methyl 2-hydroxy-2,2-diphenylacetate

HRID 551369

반응식

HRID 551369 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.C[O:11][C:12](=O)[C:13]([OH:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:12](=[O:11])[C:13]([OH:26])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 66159Methyl benzilateHCID 2719711-Methyl-4-piperidinemethanolHCID 5360545Sodium2회

생성물 1

HCID 297051(1-Methylpiperidin-4-yl)methyl 2-hydroxy-2,2-diphenylacetate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

(1-Methyl-piperidin-4-yl)-methanol (2.58 g, 20 mmol) and hydroxy-diphenyl-acetic acid methyl ester (9.69 g, 40 mmol) are suspended in toluene (65 ml). Molecular sieve 4A (1 g) is added and the mixture is stirred at room temperature for 10 minutes. Sodium (0.08 g) is added and the reaction mixture stirred at 80° C. for 3 hours. Additional sodium (0.1 g) is then added and heating maintained at 80° C. for 18 hours. The reaction mixture is cooled to room temperature, solid filtered off, and washed with ethylacetate. The filtrate is washed once with saturated aqueous NaHCO3 solution (50 ml) and twice with aqueous HCl 1M (25 ml each). The combined acidic aqueous layers are basified with saturated aqueous NaHCO3 solution and solid NaHCO3, the resulting precipitate is removed by filtration, drying under vacuum gives the title product as a white solid (M+H)+:340.09.

후처리

  1. stirringthe reaction mixture stirred at 80° C. for 3 hours
  2. temperatureheating
  3. temperaturemaintained at 80° C. for 18 hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. filtrationsolid filtered off
  6. washwashed with ethylacetate
  7. washThe filtrate is washed once with saturated aqueous NaHCO3 solution (50 ml) and twice with aqueous HCl 1M (25 ml each)
  8. customthe resulting precipitate is removed by filtration
  9. customdrying under vacuum

출처 및 근거

ORD 기록
ord-923f38430db5478eb4cdc55ba45c1ada
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947730B2

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