Diisopropylamine → HCID 11255310, compound
Reaction equation
N(C(C)C)C(C)C.[CH2:8]([Li])CCCCC.[PH:15](=[O:21])([O-])[O:16][CH:17](C)C.[O:22]=[C:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1[CH2:39][O:38]CC1>>[C:31]([O:30][C:28](=[O:29])[NH:24][CH2:25][CH2:26][CH2:27][C:23](=[O:22])[CH2:8][P:15]([O:38][CH3:39])([O:16][CH3:17])=[O:21])([CH3:34])([CH3:33])[CH3:32]Participants
Conditions
- Temperature
- -60 °C
Procedure
To a stirred solution of iPr2NH (2.99 mL, 21.8 mmol, 1.35 equiv.) in THF, cooled to −10° C., Hexyl Lithium (8.79 mL, 20.0 mmol, 1.24 equiv.) was slowly added. The reaction mixture was cooled to −60° C., Dimethylmethyl phosphonate (2.20 mL, 20.9 mmol, 1.29 equiv.) was added and stirred for 1 h, the temperature was raised to −40° C., compound 2a (3.0 g, 16.2 mmol, 1.0 equiv.) was introduced to the reaction mixture and stirring was continued for further 1 h. After consumption of the starting material, 2N H2SO4 solution (20 mL) was added slowly to the reaction and stirred at 0° C. for 15 minutes. The aqueous layer was extracted with EtOAc (2×25 mL). The combined organic extracts were washed with water (25 mL), brine (25 ml), dried over Na2SO4, filtered and evaporated under reduced pressure to afford compound 3a as a brown liquid (5.0 g, crude).
Workup
- temperaturethe temperature was raised to −40° C.
- stirringstirring
- waitwas continued for further 1 h
- customAfter consumption of the starting material, 2N H2SO4 solution (20 mL)
- additionwas added slowly to the reaction
- stirringstirred at 0° C. for 15 minutes
- extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
- washThe combined organic extracts were washed with water (25 mL), brine (25 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-291cda1a440149fca3c2ac28db50157b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901144B2
Reaction notes
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