Water → HCID 64452739, compound
Reaction equation
[CH:1]1([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:12]([Li])CCC.IC.O>O1CCCC1>[CH:1]1([CH2:6][N:7]2[C:11]([CH3:12])=[CH:10][CH:9]=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of EXAMPLE 63A (727 mg) in tetrahydrofuran (10 mL) was chilled to −45° C. n-Butyllithium (2.3 M solution in hexanes, 2.52 mL) was added dropwise over 5 minutes. The reaction was stirred for 1.5 hours, during which time the temperature increased to −20° C. Iodomethane (0.368 mL) was added dropwise over 3 minutes. The reaction was stirred for 30 minutes between −20 and −15° C. Water (25 mL) was added and the mixture was extracted with ethyl acetate (3×25 mL). The extracts were dried (Na2SO4), filtered, and concentrated to provide the title compound.
Workup
- additionwas added dropwise over 5 minutes
- stirringThe reaction was stirred for 30 minutes between −20 and −15° C
- extractionthe mixture was extracted with ethyl acetate (3×25 mL)
- dry with materialThe extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f5ef7924825748e5bd27849066d56aee
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266877B2
Reaction notes
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