Water → HCID 13677845, 화합물

HRID 1948366노트

반응식

HRID 1948366 반응식
Br[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].[N-:14]=[N+:15]=[N-:16].[Na+].O>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[N:14]([CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13])=[N+:15]=[N-:16]

참가 물질

6

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 12414165HCID 12414165, 화합물

생성물 1

HCID 13677845HCID 13677845, 화합물수율 100%

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate (Preparation: Izamanishi, T. et al; 1982, Chem. Pharm. Bull., 30: 3617-3623) (5.1 g) was dissolved in anhydrous DMF (20 mL) under an argon atmosphere, followed by the addition of 18-crown-6 (0.27 g) and sodium azide (2.89 g). The reaction was heated at 90° C. for twenty-three hours, then stirred overnight, slowly cooling to room temperature. The reaction was then added to deionised water (150 mL) to quench it, saturated with solid sodium chloride, and extracted with EtOAc (2×200 mL). The combined EtOAc layers were washed with brine (100 mL), dried over anhydrous MgSO4 and concentrated in vacuo, yielding the title compound (4.3 g, 100%). MS (GC-EI)[(M-N2)+]: 186 for C8H14BrN4O3.

후처리

  1. temperatureslowly cooling to room temperature
  2. customto quench it
  3. extractionsaturated with solid sodium chloride, and extracted with EtOAc (2×200 mL)
  4. washThe combined EtOAc layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6ef22dda261640d0b49346d18a7b669e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399489B2

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