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Acetic Acid → (R)-3-(2,6-dichloro-4-hydroxy-benzyl)-1-(tetrahydro-pyran-4-yl)-pyrrolidin-2-one

HRID 415991
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반응식

HRID 415991 반응식
[CH2:1]([C@@H:8]1[CH2:12]OC(=O)[N:9]1[C:14](=[O:36])[CH:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27]CC2C=CC=CC=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=O)[C:2]1C=CC=CC=1.NC1CC[O:41][CH2:40]C1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:26][C:25]1[CH:24]=[C:23]([OH:27])[CH:22]=[C:21]([Cl:35])[C:20]=1[CH2:19][C@@H:15]1[CH2:16][CH2:17][N:9]([CH:8]2[CH2:1][CH2:2][O:41][CH2:40][CH2:12]2)[C:14]1=[O:36]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 4192234-AminotetrahydropyranHCID 5049666Sodium triacetoxyborohydrideHCID 866312304-(4-(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

생성물 1

HCID 66621933(R)-3-(2,6-dichloro-4-hydroxy-benzyl)-1-(tetrahydro-pyran-4-yl)-pyrrolidin-2-one수율 71.6%

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

Treat a solution of 4-(4-(R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (Preparation 27) (10.4 g, 20 mmol) and 4-aminotetrahydropyran (2 g, 20 mmol) in dichloromethane (100 mL) with acetic acid (1 mL, 20 mmol). Stir the reaction 1 hr at room temperature then add sodium triacetoxyborohydride (12.6 g, 60 mmol) and stir for an additional 4 hr at room temperature. Quench with water and separate the organic layer. Wash with brine, dry over magnesium sulfate, filter, and remove the solvent under vacuum. Purify by silica gel column chromatography using hexanes:ethyl acetate to afford 4.93 g (57%) of desired product: MS (m/z): 434 (M+).

후처리

  1. customthe reaction 1 hr at room temperature
  2. customQuench with water
  3. customseparate the organic layer
  4. washWash with brine
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customremove the solvent under vacuum
  8. customPurify by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6b682c43ac284519884c4c9579ea6173
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088776B2

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