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N-Boc-pyrrolidine → (R)-tert-butyl 2-((1S,2S)-2-(dibenzylamino)-1-hydroxy-3-phenylpropyl)pyrrolidine-1-carboxylate

HRID 732347
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HRID 732347 반응식
C([Li])(CC)C.C1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1.[C:23]([N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[CH2:35]([N:42]([CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C@@H:43]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:44]=[O:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)C.C(O)(=O)C>[C:26]([O:25][C:23]([N:30]1[CH2:31][CH2:32][CH2:33][C@@H:34]1[C@@H:44]([OH:45])[C@@H:43]([N:42]([CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:53][C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 643455N-Boc-pyrrolidineHCID 644020SparteineHCID 9883943(alphaS)-alpha-[Bis(phenylmethyl)amino]benzenepropanalHCID 178418400CID 53628100

생성물 1

HCID 58699983(R)-tert-butyl 2-((1S,2S)-2-(dibenzylamino)-1-hydroxy-3-phenylpropyl)pyrrolidine-1-carboxylate수율 60.1%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 3283Diethyl Ether용매3회

실험 절차

Add sec-butyllithium (1.29 mL, 1.8 mmol) dropwise to a solution of (−)-sparteine (0.44 mL, 1.36 mmol) in diethyl ether (10 mL) over 3 min at −78° C. Add N-Boc-pyrrolidine (0.245 mL, 1.4 mmol) in diethyl ether (2 mL) dropwise over 10 min. Stir 2 h, add 2-(S)-dibenzylamino-3-phenylpropionaldehyde (0.69 g, 2.1 mmol) in diethyl ether (1.8 mL) over 5 min and stir 20 min. Add acetic acid (0.16 mL) and warn to room temperature. Add saturated aqueous sodium chloride (20 mL), separate layers, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a foam (0.421 g, 60%).

후처리

  1. stirringstir 20 min
  2. customwarn to room temperature
  3. customAdd saturated aqueous sodium chloride (20 mL), separate layers
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

출처 및 근거

ORD 기록
ord-96e470cbeb4340c79c3cdff538b20c9a
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07585885B2

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