Hydrochloric Acid → 1-Benzyloxycarbonyl-4-[methoxycarbonyl(ethylamino)]-piperidine

HRID 1634255

반응식

HRID 1634255 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](I)[CH3:23].[H-].[Na+].Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:22][CH3:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18677680Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

생성물 1

HCID 186777251-Benzyloxycarbonyl-4-[methoxycarbonyl(ethylamino)]-piperidine수율 97%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To 82 mg (0.28 mmol) of 1-benzyloxycarbonyl-4-(methoxycarbonylamino)piperidine from Step A and 0.045 mL (0.56 mmol) of ethyl iodide in 4 mL of DMF under nitrogen was added 22 mg (0.56 mmol) of 60% sodium hydride in mineral oil. The reaction was stirred at rt for 1 h and was then poured into water containing 1 mL of 2N hydrochloric acid and extracted twice with ether. The organic layers were each washed with a portion of brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC eluting with 50% ethyl acetate/hexanes to afford 87 mg of title compound.

후처리

  1. extractionextracted twice with ether
  2. washeach washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by FC
  6. washeluting with 50% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-7cd3bdf3043d4b89a63000f05bb27ad7
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506777B1

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