Tetrahydrofuran → tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

HRID 43600

반응식

HRID 43600 반응식
C1COCC1.[NH2:6][C@H:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]1[O:20][CH3:21].C(=O)(O)[O-].[Na+].Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>O>[CH2:31]([O:30][C:28]([NH:6][C@H:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@H:8]1[O:20][CH3:21])=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 57362389(3R,4S)-4-Amino-1-boc-3-methoxypiperidine

생성물 1

HCID 86648489tert-Butyl cis(+/-)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate수율 95%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

THF (20 mL) and water (15 mL) were added to tert-butyl cis(±)-4-amino-3-methoxypiperidine-1-carboxylate (described in Example (1e), 4.6 g, 20 mmol). The mixture was stirred, during which sodium bicarbonate (3.44 g, 40 mmol) and benzyl chloroformate (3.95 g, 22 mmol) were added at room temperature, followed by stirring for one hour. The reaction solution was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1) to obtain 6.89 g of the title compound as a colorless solid (95%).

후처리

  1. additionwere added at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1)

출처 및 근거

ORD 기록
ord-da22337b9bd14591aeccc26c79005c28
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536197B2

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