Water → HCID 13677845、化合物

HRID 1948366ノート

反応式

HRID 1948366 の反応式
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]

参加物

6

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 12414165HCID 12414165、化合物

生成物 1

HCID 13677845HCID 13677845、化合物収率 100%

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6ef22dda261640d0b49346d18a7b669e
出典データセット
uspto-grants-2013_03
特許番号
US08399489B2

反応ノート

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