2-Isocyanatooxane → HCID 9908905, compound

HRID 2180016Notes

Reaction equation

HRID 2180016 reaction equation
[O:1]1CCCC[CH:2]1[N:7]=C=O.[NH2:10][CH:11]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[CH2:12][N:13]1[CH2:20][CH:19]2[CH2:21][CH:15]([CH2:16][N:17]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18]2)[CH2:14]1>C1C=CC=CC=1>[C:2]([NH:10][CH:11]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[CH2:12][N:13]1[CH2:14][CH:15]2[CH2:21][CH:19]([CH2:18][N:17]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:16]2)[CH2:20]1)(=[O:1])[NH2:7]

Participants

4

Reactant 2

HCID 1025762-IsocyanatooxaneHCID 9885062HCID 9885062, compound

Product 1

HCID 9908905HCID 9908905, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of tetrahydro-2-pyranyl isocyanate (382 mg, 3.0 mmol) in benzene (10 mL) was added to a stirred solution of iso-propyl 7-[2-amino-2-(4-cyanophenyl)ethyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (see Example 9 above; 1.07 g; 3.0 mmol) in benzene (35 mL). The reaction mixture was stirred for 2 h at rt, after which the solvent was evaporated and the residue re-dissolved in a mixture of MeOH (27 mL) and dilute HCl (4.5 mL; 0.1 M). The resulting solution was refluxed for 3 h, before the acid was neutralized (NaHCO3) and the MeOH removed by evaporation to give a precipitate which was collected and recrystallized from IPA to give the title compound in 67% yield.

Workup

  1. customafter which the solvent was evaporated
  2. dissolutionthe residue re-dissolved in a mixture of MeOH (27 mL) and dilute HCl (4.5 mL; 0.1 M)
  3. temperatureThe resulting solution was refluxed for 3 h, before the acid
  4. customthe MeOH removed by evaporation
  5. customto give a precipitate which
  6. customwas collected
  7. customrecrystallized from IPA

Sources & evidence

ORD record
ord-33a88ec04b6a41dba1e218d3e4c27b5c
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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