Diisopropylethylamine → (2S)-2-[[N-(2-Oxo-3,3-diphenylpropyl)-(2-methoxybenzyl)amino]methyl]pyrrolidine-1-carboxylic acid benzyl ester

HRID 1006324

반응식

HRID 1006324 반응식
Br[CH2:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.[CH2:27]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][NH:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[O:51][CH3:52])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[CH2:27]([O:34][C:35]([N:37]1[CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:42][N:43]([CH2:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[O:51][CH3:52])=[O:36])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27946353-Bromo-1,1-diphenylacetoneHCID 69745936(2S)-2-[(2-methoxybenzylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 69746794(2S)-2-[[N-(2-Oxo-3,3-diphenylpropyl)-(2-methoxybenzyl)amino]methyl]pyrrolidine-1-carboxylic acid benzyl ester수율 6.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Bromo-1,1-diphenyl-2-propanone (12.7 g) and N,N-diisopropylethylamine (15.7 ml) were added successively to a solution of (2S)-2-[(2-methoxybenzylamino)methyl]pyrrolidine-1-carboxylic acid benzyl ester (15.6 g) in tetrahydrofuran (156 ml) at 0° C. After being stirred at room temperature for 2 hours, the mixture was poured into ice-water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (3:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give a colorless syrup of (2S)-2-[[N-(2-oxo-3,3-diphenylpropyl)-N-(2-methoxybenzyl)amino]methyl]pyrrolidine-1-carboxylic acid benzyl ester (1.51 g).

후처리

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (3:1)
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-55cea16af00843c3ae7ea8c050107c96
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787543B2

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