Allyl iodide → HCID 68666328, compound

HRID 1443402Notes

Reaction equation

[CH:1]([N-]C(C)C)([CH3:3])[CH3:2].[Li+].[C:9]([O:13][C:14]([N:16]1[CH:20]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17]1=[O:29])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(I)C=C>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]([CH2:3][CH:1]=[CH2:2])[C:17]1=[O:29])=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of freshly prepared lithium diisopropylamide (2.80 mmol) in 10 mL of THF was added dropwise into a solution of N-tert-butyloxycarbonyl-5-(4-cyanophenyl)-2-pyrrolidinone (763 mg, 2.67 mmol) in 10 mL of THF at −78° C. After stirring for 1 hr at −78° C., allyl iodide (488 μL, 5.33 mmol) was added. The mixture was stirred at −78° C. for 1 hr, and then quenched with 5.0 mL of sat'd NH4Cl solution. The mixture was poured into a mixture of brine (20 mL) and CH2Cl2 (20 mL), and the aqueous layer was separated and extracted with CH2Cl2 (3×20 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 1:4 v/v EtOAc/hexanes as the eluant gave 745 mg (86%) of the title compound: 1H NMR δ 1.35 (s, 9H), 1.99-2.05 (m, 1H), 2.21-2.29 (m, 1H), 2.63-2.76 (m, 2H), 5.06-5.11 (m, 2H), 5.17-5.20 (m, 1H), 5.68-5.77 (m, 1H), 7.32 (d, J=8.2, 2H), 7.67 (d, J=8.4, 2H).

Workup

stirringThe mixture was stirred at −78° C. for 1 hr
customquenched with 5.0 mL of sat'd NH4Cl solution
additionThe mixture was poured 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 MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-447d060726fd4d08b58628d5fe68f2d3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659294B2

Reaction notes

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