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

HRID 732374ノート

反応式

HRID 732374 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-786c264887874d0a88f77749394f9582
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

読み込み中…