Ammonium Chloride → 2-(R)-(2-(S)-Dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732374

반응식

HRID 732374 반응식
C([Li])(CC)C.C1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH3:36])[CH3:35])=[O:29])([CH3:26])([CH3:25])[CH3:24].[CH2:37]([N:44]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C@@H:45]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH:46]=[O:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[Cl-].[NH4+]>C(OCC)C.C(OCC)(=O)C>[C:23]([O:27][C:28]([N:30]1[C:31]([CH3:36])([CH3:35])[CH2:32][CH2:33][C@@H:34]1[C@@H:46]([OH:47])[C@@H:45]([N:44]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

참가 물질

8

반응물 5

HCID 25517Ammonium ChlorideHCID 644020SparteineHCID 9883943(alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanalHCID 57366408tert-Butyl 2,2-dimethylpyrrolidine-1-carboxylateHCID 178418400CID 53628100

생성물 1

HCID 688152432-(R)-(2-(S)-Dibenzylamino-1-(S)-hydroxy-3-phenylpropyl)-5,5-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester수율 12%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 8857Ethyl Acetate용매

실험 절차

Add sec-butyllithium (2.9 mL, 2.1 mmol) dropwise to a solution of freshly distilled (−)-sparteine (1 mL, 4.3 mmol) in diethyl ether (25 mL) over 3 min at −78° C. Add 2,2-dimethylpyrrolidine-1-carboxylic acid tert-butyl ester (645 mg, 3.2 mmol) in diethyl ether (2 mL) dropwise over 10 min. Stir 2 h, add 2-(S)-dibenzylamino-3-phenylpropionaldehyde (967 mg, 2.9 mmol) in diethyl ether (2 mL) over 5 min and stir 20 min. Add saturated aqueous ammonium chloride solution and ethyl acetate and let warm to room temperature, separate the layers, extract the aqueous layer with ethyl acetate, wash the organic layer with saturated aqueous sodium chloride solution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 4:1 hexanes:ethyl acetate) to give the title compound as a colorless oil (182 mg, 12%).

후처리

  1. stirringstir 20 min
  2. customseparate the layers
  3. extractionextract the aqueous layer with ethyl acetate
  4. washwash the organic layer with saturated aqueous sodium chloride solution
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 4:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-786c264887874d0a88f77749394f9582
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

연결된 노트

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