Potassium Cyanide → (S)-Benzyl 3-cyanopyrrolidine-1-carboxylate

HRID 2087088ノート

反応式

HRID 2087088 の反応式
S([C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:26]#[N:27].[K+].[Cl-].[Na+].O.O>CS(C)=O>[C:26]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:12]1)#[N:27]

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 23713072Sodium chloride dihydrateHCID 671827093-Tosyl-Cbz-(R)-Pyrrolidine

生成物 1

HCID 44828648(S)-Benzyl 3-cyanopyrrolidine-1-carboxylate収率 70.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

3-Tosyl-Cbz-(R)-pyrrolidine (20.4 g, 0.05 mol) was dissolved in DMSO (54 mL), followed by the addition of KCN (5.3 g, 0.08 mol). The reaction mixture was stirred for 5 h at 80° C. The solution was cooled to room temperature and brine/H2O (90 mL) (1/1, v/v) was added. The aqueous solution was extracted with ethyl acetate. The organic extracts were dried over MgSO4, and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1, v/v) to afford 8.13 g (65% yield) of the desired product as an oil.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes (1/1

出典と根拠

ORDレコード
ord-82a8e1471e734796aa781be9dd8f2219
出典データセット
uspto-grants-2004_04
特許番号
US06727368B1

反応ノート

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