Water → Benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate

HRID 518805노트

반응식

HRID 518805 반응식
[BH4-].[Na+].[I-].[CH2:4]([O:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][N+:24]([CH3:27])=[CH:23][C:22]=2[O:28][CH3:29])=[CH:17][C:16]=1[O:30][CH:31]([CH3:33])[CH3:32])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:29][O:28][C:22]1[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[O:11][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[C:16]([O:30][CH:31]([CH3:33])[CH3:32])[CH:17]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866979754-[4-{[(Benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide

생성물 1

HCID 86697977Benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate수율 53.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

486 mg of NaBH4 are added, in portions, to a suspension of 4.57 g of 4-[4-{[(benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide in 100 ml of ethanol brought to 5° C. The reaction medium is stirred for 1 h 30 at ambient temperature. 50 ml of water, 50 ml of a saturated aqueous sodium bicarbonate solution and 100 ml of ethyl acetate are added. The two phases are separated, and the aqueous phase is washed with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and (MeOH+10% NH4OH) (99/1 to 90/10). 1.87 g of benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate are obtained in the form of an orangey-coloured oil.

후처리

  1. custombrought to 5° C
  2. customThe two phases are separated
  3. washthe aqueous phase is washed with twice 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of dichloromethane and (MeOH+10% NH4OH) (99/1 to 90/10)

출처 및 근거

ORD 기록
ord-066d47a5843142f4abec23566e5218ba
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115140B2

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