Ammonium Chloride → Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

HRID 1068177ノート

反応式

HRID 1068177 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[N:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylate

生成物 1

HCID 18187701Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2.10 g (10.0 mmol) of 1-(t-butoxycarbonyl)-4-cyanopiperidine (from Step A), 1.95 g (30.0 mmol) of sodium azide and 1.60 g (30.0 mmol) of ammonium chloride in 20 mL of DMF was stirred at 100° C. for 20 h. The mixture was cooled and partitioned between 200 mL of CH2Cl2 and 200 mL of 1.0N HCl and the layers were separated. The organic layer was washed with 200 mL of H2O, dried over MgSO4 and concentrated. Flash chromatography on 50 g of silica gel using 4:1 v/v CH2Cl2/EtOAc+1% HOAc, then 2:1 v/v CH2Cl2/EtOAc+1% HOAc as the eluant afforded 1.51 g (60%) of the title compound: 1H NMR (500 MHz) δ1.49 (s, 9H), 1.83-1.89 (m, 2H), 2.13-2.15 (m, 2H), 2.96-3.04 (m, 2H), 3.13-3.36 (m, 1H), 4.14-4.22 (m, 2H).

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between 200 mL of CH2Cl2 and 200 mL of 1.0N HCl
  3. customthe layers were separated
  4. washThe organic layer was washed with 200 mL of H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-c70a2b7146c246568522bd680f42ea76
出典データセット
uspto-grants-2001_06
特許番号
US06248755B1

反応ノート

読み込み中…