Triethylsilane → ethyl 2-(5-cyclohexyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189532Notes

Reaction equation

HRID 1189532 reaction equation
[CH:1]1([C:7]2[N:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([CH3:12])=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[N:38]1([S:43]([C:46]2[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=2[CH:48]=O)(=[O:45])=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH:1]1([C:7]2[N:8]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([CH3:12])=[C:10]([CH2:48][C:47]3[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=3[S:43]([N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)(=[O:44])=[O:45])[CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 573845822-(Pyrrolidin-1-ylsulfonyl)benzaldehydeHCID 67237997ethyl 2-(2-cyclohexyl-5-methyl-1H-pyrrol-1-yl)acetate

Product 1

HCID 53247598ethyl 2-(5-cyclohexyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateYield 34%

Procedure

was followed using ethyl 2-(2-cyclohexyl-5-methyl-1H-pyrrol-1-yl)acetate (1.00 g, 4.01 mmol), triethylsilane (1.92 mL, 12.0 mmol), trimethylsilyl trifluoromethanesulfonate (1.45 mL, 8.02 mmol) and 2-(pyrrolidin-1-ylsulfonyl)benzaldehyde (0.960 g, 4.01 mmol) to afford ethyl 2-(5-cyclohexyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (642 mg, 1.36 mmol, 34% yield).

Sources & evidence

ORD record
ord-b88bfaa949fc468f85afaa37b7f13420
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

Loading…