Sodium Cyanide → HCID 178454087、化合物

HRID 628356ノート

反応式

HRID 628356 の反応式
CS(O[C@H:6]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[C-:18]#[N:19].[Na+]>CN(C=O)C>[C:18]([C@H:6]1[CH2:9][C@H:8]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1)#[N:19]

参加物

4

反応物 2

HCID 8929Sodium Cyanide2 回HCID 178454135HCID 178454135、化合物

生成物 1

HCID 178454087HCID 178454087、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

cis-3-[(tert-Butoxycarbonyl)amino]cyclobutyl methanesulfonate (0.200 g, 0.754 mmol) in DMF (3 mL) was treated with NaCN (55 mg, 1.13 mmol, Aldrich) and the reaction was heated in the microwave to 140° C. for 10 minutes, followed by stirring overnight at 125° C. with an additional 55 mg (1.13 mmol) of NaCN having been added. The reaction mixture was partitioned between saturated NaHCO3 solution and EtOAc. The aqueous layer was extracted three additional times with EtOAc. The combined extracts were dried over sodium sulfate, decanted, and the solvent was removed in vacuo. Flash chromatography, eluting with a gradient from 0-50% EtOAc in hexanes, afforded tert-butyl (trans-3-cyanocyclobutyl)carbamate. Yield: (61 mg, 41%).

後処理

  1. additionbeen added
  2. customThe reaction mixture was partitioned between saturated NaHCO3 solution and EtOAc
  3. extractionThe aqueous layer was extracted three additional times with EtOAc
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. customthe solvent was removed in vacuo
  7. washFlash chromatography, eluting with a gradient from 0-50% EtOAc in hexanes

出典と根拠

ORDレコード
ord-d6736b86da054e7bb6cf4d5812f37937
出典データセット
uspto-grants-2016_04
特許番号
US09309246B2

反応ノート

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