Reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([C:12](O)=[O:13])[CH2:6][CH2:5]2.B.C1COCC1.O.C([O-])(O)=O.[Na+]>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([CH2:12][OH:13])[CH2:6][CH2:5]2Participants
6
Conditions
- Temperature
- 45 °C
Procedure
To a solution of (2R)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acid (Example 7, 19.5 mmol, 1.0 eq.) in THF (45 mL) at 10° C. was added dropwise a solution of borane-THF complex (1M in THF, 23.4 mmol, 1.2 eq). The resulting reaction mixture was stirred at 45° C. for 1.5 hours and was then cooled to 10° C. Next, water was added followed by saturated NaHCO3 solution. The resulting two-phase mixture was separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, concentrated to afford the product as a white solid in quantitative yield that was used without further purification. GC-MS m/z 290 (M+)
Workup
- customThe resulting reaction mixture
- temperaturewas then cooled to 10° C
- customThe resulting two-phase mixture was separated
- extractionthe aqueous phase was extracted with ethyl acetate
- washThe combined organic extracts were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d408dc4064424a799a8277a775e39f72
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06919371B2
Linked notes
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