Ethanol → (7S)-7-(4-bromophenyl)-1,3-diazaspiro[4.4]nonane-2,4-dione
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=O)[CH2:9]2)=[CH:4][CH:3]=1.[C-]#N.[K+].[C:17](=[O:20])([O-])[O-].[NH4+:21].[NH4+:22].C[CH2:24][OH:25]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10]3([NH:22][C:24](=[O:25])[NH:21][C:17]3=[O:20])[CH2:9]2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of (S)-3-(4-bromophenyl)cyclopentanone (I-1A, 4.9 g, 20.49 mmol) and potassium cyanide (1.935 g, 29.7 mmol) in EtOH (40 mL) and water (20 mL) in a glass pressure vessel was added ammonium carbonate (4.92 g, 51.2 mmol). The reaction vessel was sealed and placed in an oil bath heated at 80° C. for 24 hours, resulting in the formation of a white solid. After cooling the reaction vessel in an ice bath, the vessel was opened and 30 ml of water was added resulting in the formation of additional solids. The solids were collected by filtration, washed twice with 5 ml water, and then dried under high vacuum. The two batches were combined to provide 13.9 g of (7S)-7-(4-bromophenyl)-1,3-diazaspiro[4.4]nonane-2,4-dione) which were used for subsequent reactions without further purification. HPLC retention time=0.82 min (Condition G) LC/MS M+Na=331, 2M+H=619.
Workup
- customThe reaction vessel was sealed
- customplaced in an oil bath
- customresulting in the formation of a white solid
- temperatureAfter cooling the reaction vessel in an ice bath
- customresulting in the formation of additional solids
- filtrationThe solids were collected by filtration
- washwashed twice with 5 ml water
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-91fd891fb6f7479dbbbde96eeb917f0f
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359286B2
Reaction notes
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