Sodium Cyanide → tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate

HRID 245916ノート

反応式

HRID 245916 の反応式
[C-:1]#[N:2].[K+].[C-]#N.[Na+].[C:7]([O:11][C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][C@H:17]([CH2:20]OS(C)(=O)=O)[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CN(C=O)C>[C:7]([O:11][C:12](=[O:13])[NH:14][C@H:15]1[CH2:19][CH2:18][C@@H:17]([CH2:20][C:1]#[N:2])[CH2:16]1)([CH3:10])([CH3:9])[CH3:8]

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 9032Potassium CyanideHCID 18453418rac-tert-butyl N-[(1R,3S)-3-[(methanesulfonyloxy)methyl]cyclopentyl]carbamate

生成物 1

HCID 20729728tert-butyl N-[(1S,3R)-3-(cyanomethyl)cyclopentyl]carbamate収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

In a round-bottomed flask, methanesulfonic acid (cis)-3-tert-butoxycarbonylamino-cyclopentylmethyl ester (crude from Step 4, 779 mg) was dissolved in DMF (5 ml). Potassium cyanide (277 mg, 4.25 mmol) was added and the reaction mixture was stirred at 80° C. overnight. Sodium cyanide (104 mg, 2.12 mmol) was added and the reaction mixture was stirred at 80° C. for 48 h. The reaction was cooled to room temperature, quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 190 mg (38%, 2 steps) of (cis-3-cyanomethyl-cyclopentyl)-carbamic acid tert-butyl ester as a light yellow oil.

後処理

  1. stirringthe reaction mixture was stirred at 80° C. for 48 h
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with diethyl ether (2×)
  5. washThe combined organic layers were washed twice with water and once with brine
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)

出典と根拠

ORDレコード
ord-76c9e5024f61495c9332d39627a483d1
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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