Nitrogen → HCID 86757398, compound

HRID 1596457Notes

Reaction equation

HRID 1596457 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH2:2]2.CS(O[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].N#N>CC#N>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][N:7]2[CH2:8][CH:1]3[CH2:9][CH:5]([CH2:4][N:3]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH2:2]3)[CH2:6]2)=[CH:24][CH:25]=1)#[N:30]

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 226326484-Cyanophenethyl methanesulfonateHCID 53914229HCID 53914229, compound

Product 1

HCID 86757398HCID 86757398, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

iso-Propyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.06 g; 5 mmol; see Example H above) was added to a stirred suspension of 4-cyanophenethyl methanesulfonate (1.13 g; 5 mmol; from step (a) above) and K2CO3 (0.96 g; 7 mmol) in MeCN (5 mL) under an inert atmosphere (N2), and the reaction mixture was stirred for 10 h. The solvent was evaporated and the residue partitioned between DCM and NaHCO3 (aq.). The organic layer was separated, dried and concentrated. Purification using column chromatography (DCM:MeOH; 19:1) gave the title compound in a 88% yield.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between DCM and NaHCO3 (aq.)
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-aaa6d9e2a3ca4cd18d12ec4a47189eed
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

Loading…