Lithium diisopropylamide → HCID 68666045, compound
Reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:13][C:14]([N:16]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH2:19][C@H:18]([CH2:29][CH:30]=[CH2:31])[C:17]1=[O:32])=[O:15])([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[C:9]([O:13][C:14]([N:16]1[C@H:20]([C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)[CH2:19][C@H:18]([CH2:29][CH:30]=[CH2:31])[C:17]1=[O:32])=[O:15])([CH3:12])([CH3:11])[CH3:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of freshly prepared lithium diisopropylamide (0.75 mmol) in 5 mL of THF was added dropwise into a solution of trans N-tert-butyloxycarbonyl-5-(4-cyanophenyl)-3-(2-propenyl)-2-pyrrolidinone (223 mg, 0.68 mmol) in 5 mL of THF at −78° C. After stirring at −78° C. for 1 hr, the reaction was quenched by adding 5.0 mL of sat'd NH4Cl solution. The mixture was allowed to warm up to rt, and poured into a mixture of brine (20 mL) and CH2Cl2 (20 mL). The aqueous layer was separated and extracted with CH2Cl2 (3×20 mL). Organic layers were combined, dried over Na2SO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 1:3 v/v EtOAc/hexanes as the eluant gave 103 mg (46%) of the title compound and 120 mg (54%) of starting material: 1H NMR δ 1.24 (s, 9H), 1.50-1.57 (m, 1H), 2.22-2.28 (m, 1H), 2.56-2.77 (m, 3H), 4.94-5.07 (m, 3H), 5.71-5.78 (m, 1H), 7.36 (d, J=8.2, 2H), 7.66 (d, J=8.2, 2H).
Workup
- customthe reaction was quenched
- additionby adding 5.0 mL of sat'd NH4Cl solution
- temperatureto warm up to rt
- additionpoured into a mixture of brine (20 mL) and CH2Cl2 (20 mL)
- customThe aqueous layer was separated
- extractionextracted with CH2Cl2 (3×20 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7ce088d5b8084c2094ab7b365003b99e
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659294B2
Reaction notes
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