Water → cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine

HRID 344291ノート

反応式

HRID 344291 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]OS(C)(=O)=O)[C@H:10]([OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[N:21]([CH2:14][C@H:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@H:10]1[OH:20])=[N+:22]=[N-:23]

参加物

6

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

生成物 1

HCID 86657830cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine収率 92.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of cis-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine (4.44 g) in dimethylformamide (60 ml) were added sodium azide (1.4 g) and ammonium chloride (1.15 g), and the resulting mixture was stirred at 60° C. for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 3.4 g of cis-4-azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine.

後処理

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

出典と根拠

ORDレコード
ord-97df34546f294ddb8456e8f561dab525
出典データセット
uspto-grants-1999_01
特許番号
US05864039

反応ノート

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