Acetic Acid → 2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol
Reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([C:11](=[O:21])[C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>CO>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH:11]([OH:21])[C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
The product of step e) (325 mg, 0.76 mmol) was dissolved in MeOH (10 ml) and treated with NaBH4 (289 mg, 7.6 mmol) at 0° C. Next, the reaction was warmed to 22° C. and, after 2 hours, AcOH was added dropwise until gas evolution ceased. The quenched reaction mixture was slowly poured saturated NaHCO3 (100 ml). The aqueous mixture was extracted with EtOAc (2×50 ml), dried (MgSO4) and concentrated providing the subtitle product (298 mg, 91%). MS calculated for C16H15Br2NOS+H 430, observed 428, 430, 432.
Workup
- customThe quenched reaction mixture
- extractionThe aqueous mixture was extracted with EtOAc (2×50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4fc0e99798a44a0bbc752e0e24c99706
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423056B2
Reaction notes
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