Lithium diisopropylamide → HCID 86585015, compound

HRID 1738894Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[C:28]1([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([CH:41]=[CH:42][CH:43]=[O:44])[CH2:37][CH2:36]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1.C1CCCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[CH:12]=[C:11]2[C:42](=[CH:41][CH:38]2[CH2:37][CH2:36][N:35]([CH2:34][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:40][CH2:39]2)[CH2:43][OH:44])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-phenylsulfonyl-6-methyl indole (1.18 g, 4.34 mmol) in 30 ml of dry THF was cooled to -78° C. and treated with 3.5 ml (5.2 mmol) of 1.5 M lithium diisopropylamide in cyclohexane at -78° C. After stirring at -78° C. for 1 hour, a solution of 3-[1-(phenylmethyl)-4-piperidinyl]-2-propenal (1.0 g, 4.36 mmol) in 5 ml of dry THF was added at -78° C. and stirred at that temperature for 40 minutes. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 2.23 g of an orange oil. The oil was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give 1.0 g of the title compound as a yellow oil.

Workup

stirringstirred at that temperature for 40 minutes
customThe mixture was quenched with water
extractionextracted with chloroform
customThe organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-5f49b9fb44bf489ca88e35f5e333d125
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965574

Reaction notes

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