Sodium Cyanide → HCID 178454087, 화합물

HRID 628356노트

반응식

HRID 628356 반응식
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]

참가 물질

4

반응물 2

HCID 8929Sodium Cyanide2회HCID 178454135HCID 178454135, 화합물

생성물 1

HCID 178454087HCID 178454087, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
140 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d6736b86da054e7bb6cf4d5812f37937
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309246B2

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