Water → HCID 89498784, compound
Reaction equation
[C:1]12([CH2:11][N:12]3[CH:16]=[CH:15][CH:14]=[N:13]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:17]([Li])CCC.IC.O>O1CCCC1>[C:1]12([CH2:11][N:12]3[C:16]([CH3:17])=[CH:15][CH:14]=[N:13]3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of EXAMPLE 3A (869 mg) in tetrahydrofuran (10 mL) was chilled to −45° C. n-Butyllithium (2.3 M solution in hexanes, 2.10 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 (0.305 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-8b8a2201f4ce46cda5beff593b32dc3c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889675B2
Reaction notes
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