Water → HCID 58428106, compound
Reaction equation
[OH:1][C:2]1[C:6]2([CH2:11][CH2:10][N:9]([O:12][CH3:13])[CH2:8][CH2:7]2)[N:5]([O:14]COC)[C:4](=[O:18])[C:3]=1[C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=1[CH3:27].Br[Si](C)(C)C.O>ClCCl>[OH:14][N:5]1[C:6]2([CH2:7][CH2:8][N:9]([O:12][CH3:13])[CH2:10][CH2:11]2)[C:2]([OH:1])=[C:3]([C:19]2[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])[C:4]1=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-hydroxy-8-methoxy-1-methoxymethoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound P2ii.6 obtained in analogy to preparation example 11, step 5) (500 mg, 1.33 mmol) in dichloromethane (10 ml) under argon atmosphere at 0° C. was added 3 {acute over (Å)} molecular sieves (0.5 g), followed by bromotrimethylsilane (1.72 ml, 2.03 g, 13.28 mmol) dropewise and the reaction mixture was stirred at 0° C. for one hour and at room temperature for 48 hours. The mixture was poured on cold water, the water layer saturated with sodium chloride and thoroughly extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (ethyl acetate). Yield: 40 mg of 1,4-dihydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2ii.4) as a white solid, mp 152-154° C.
Workup
- extractionthe water layer saturated with sodium chloride and thoroughly extracted with dichloromethane
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel (ethyl acetate)
Sources & evidence
- ORD record
- ord-bdb1d9bc56354935ae3ec0e3b1584b9b
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018135B2
Reaction notes
Loading…