Hydrochloric Acid → (R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH:13]=[O:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl.O>O1CCCC1.C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][OH:14])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To an ice cold mixture of (S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (2.00 g, 8.72 mmol) in tetrahydrofuran (15 mL) and isopropanol (15 mL) was added sodium borohydride (0.99 g, 26.17 mmol). After addition was complete the mixture was stirred at 0° C. for 1 h. Upon completion of the reaction 1N aqueous hydrochloric acid (10 mL) was slowly added. The mixture was poured into water and extracted with ethyl acetate (3×30 mL). The combined organic fractions were washed with a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained (R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.88 g, 93%) as a colorless oil and was used without further purification: LR-ES-MS m/z calculated for C11H21NO4 [M]+ 231, observed 232 [M+H]+.
Workup
- additionAfter addition
- additionwas slowly added
- extractionextracted with ethyl acetate (3×30 mL)
- washThe combined organic fractions were washed with a saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
Sources & evidence
- ORD record
- ord-a2b07bf43b7a4a938fb6c9aa3aad7dce
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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