HCID 67819743, compound → HCID 57192079, compound

HRID 486787Notes

Reaction equation

C([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[C:13]3[CH2:20][C@@H:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:22][C@@H:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.C([Li])CCC>>[C:18]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][CH2:10][C@H:11]3[CH2:22][C@H:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:20][C:13]=1[C:12]=23)#[N:19]

Participants

Reactant 2

HCID 67819743HCID 67819743, compound

HCID 178418339Butyllithium

Product 1

HCID 57192079HCID 57192079, compoundYield 86.9%

Procedure

The procedure of Example 7E was followed using 2.5 g (6.5 mmol) of (2aS,4S)-1-benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole and 8.1 ml (13 mmol) n-butyl lithium to provide 1.6 g of an oil. Chromatography of the oil over silica gel with EtOAc as eluent gave 1 g (54%) of product as an oil.

Sources & evidence

ORD record: ord-bf1cdb791dc145f489126e8ee063d8f3
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292766

Reaction notes

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