Sodium Cyanide → HCID 178454087, compound

HRID 628356Notes

Reaction equation

HRID 628356 reaction equation
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]

Participants

4

Reactant 2

HCID 8929Sodium Cyanide2×HCID 178454135HCID 178454135, compound

Product 1

HCID 178454087HCID 178454087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d6736b86da054e7bb6cf4d5812f37937
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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