Sodium Cyanide → HCID 67002293, compound

HRID 2191587Notes

Reaction equation

HRID 2191587 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:17]([OH:20])([CH3:19])[CH3:18])[CH2:10][CH2:11]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-]#N.[Na+]>CN1C(=O)CCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][O:20][C:17]1([CH3:18])[CH3:19])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86659501HCID 86659501, compound

Product 1

HCID 67002293HCID 67002293, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methanesulfonic acid 3-tert-butoxycarbonylamino-4-hydroxy-4-methyl-pentyl ester (627 mg, 2.0 mmol, crude from step 2) in NMP (5 mL) was added sodium cyanide (0.98 g, 20 mmol). The reaction mixture was heated at 85° C. overnight then cooled to room temperature and partitioned between water and diethyl ether. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography (20% to 50% EtOAc/hexanes) to afford 268 mg (62%) of (2,2-dimethyl-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. temperaturethen cooled to room temperature
  2. custompartitioned between water and diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by SiO2 chromatography (20% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3040f10c94da48e9b2e18f69c0bd3627
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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