Isopropanol → (4S,5S)-2-Allyl-2-isopropoxy-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine
Reaction equation
[CH2:1]([Si:4]1(Cl)[N:8]([CH3:9])[C@@H:7]([CH3:10])[C@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:5]1)[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:25][CH:26]([OH:28])[CH3:27]>C(Cl)Cl>[CH2:1]([Si:4]1([O:28][CH:26]([CH3:27])[CH3:25])[N:8]([CH3:9])[C@@H:7]([CH3:10])[C@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:5]1)[CH:2]=[CH2:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (2.08 g, 7.8 mmol) in methylene chloride (25 mL) was added triethylamine (1.2 mL, 8.6 mmol). 2-Propanol (0.6 mL, 7.8 mmol) was added slowly by syringe and the mixture was allowed to stir for 12 hours. The methylene chloride was removed by distillation and pentane (20 ml) was added to the residue. The mixture was stirred for 3 hours. The mixture was then filtered through a pad of celite. The filtrate was concentrated to afford an oil which was distilled under reduced pressure (b.p. ˜72° C., ˜0.2 mm Hg) to yield 1.08 g (48%) of (4S,5S)-2-Allyl-2-isopropoxy-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine as a ˜2:1 mixture of diastereomers.
Workup
- customThe methylene chloride was removed by distillation and pentane (20 ml)
- additionwas added to the residue
- stirringThe mixture was stirred for 3 hours
- filtrationThe mixture was then filtered through a pad of celite
- concentrationThe filtrate was concentrated
- customto afford an oil which
- distillationwas distilled under reduced pressure (b.p. ˜72° C., ˜0.2 mm Hg)
Sources & evidence
- ORD record
- ord-bd6952b0f8664b54b33a0993db6fb582
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534905B2
Reaction notes
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