1-Chloroethyl chloroformate → (5-Methylthiophen-2-yl)(5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)methanone hydrochloride
Reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][C:23]2([CH2:29][N:28]([C:30]([C:32]3[S:33][C:34]([CH3:37])=[CH:35][CH:36]=3)=[O:31])[CH2:27][CH2:26][O:25]2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[ClH:1].[CH3:37][C:34]1[S:33][C:32]([C:30]([N:28]2[CH2:29][C:23]3([CH2:22][NH:21][CH2:24]3)[O:25][CH2:26][CH2:27]2)=[O:31])=[CH:36][CH:35]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Chloroethyl chloroformate (0.508 mL) was added dropwise to a solution of (2-benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-8-yl)(5-methylthiophen-2-yl)methanone (example 33, step g) (1.5 g) in acetonitrile (30 mL) at 0° C. The mixture was then heated at reflux for 1 hour under nitrogen. The solvent was removed under reduced pressure and the residue dissolved in methanol (50 mL). This solution was heated at reflux under nitrogen for 30 minutes. The solvent was removed under reduced pressure and the residue triturated with ethyl acetate (40 mL) and then with acetonitrile (7 mL) to yield the subtitled compound. Yield 0.29 g.
Workup
- temperatureThe mixture was then heated
- temperatureat reflux for 1 hour under nitrogen
- customThe solvent was removed under reduced pressure
- dissolutionthe residue dissolved in methanol (50 mL)
- temperatureThis solution was heated
- temperatureat reflux under nitrogen for 30 minutes
- customThe solvent was removed under reduced pressure
- customthe residue triturated with ethyl acetate (40 mL)
Sources & evidence
- ORD record
- ord-5a20533020cd4b0990b76f78058ce952
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148373B2
Reaction notes
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