Triethylsilane → HCID 14107793, compound

HRID 2291826Notes

Reaction equation

HRID 2291826 reaction equation
C([SiH](CC)CC)C.[CH3:8][N:9]1[C@H:23]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24]=3[C:21]([CH2:22]2)=[CH:20][NH:19]4)=[CH:12][C@@H:11]([CH2:25][C:26]#[N:27])[CH2:10]1>C(O)(C(F)(F)F)=O>[CH3:8][N:9]1[C@H:23]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24]=3[C:21]([CH2:22]2)=[CH:20][NH:19]4)=[CH:12][C@@H:11]([CH2:25][C:26]#[N:27])[CH2:10]1.[CH3:8][N:9]1[C@H:23]2[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24]=3[C@H:21]([CH2:22]2)[CH2:20][NH:19]4)=[CH:12][C@@H:11]([CH2:25][C:26]#[N:27])[CH2:10]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 10515696HCID 10515696, compound

Product 2

HCID 10515696HCID 10515696, compoundHCID 14107793HCID 14107793, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(5β,8β)-9,10-didehydro-6-methylergoline-8-acetonitrile was prepared according to the method of Troxler et al., Helv. Chim. Acta 1968, 51, 1060. Following procedures essentially as described in Example 1, a mixture of 10 ml of TFA, 1.82 g (15.7 mmol) of triethylsilane and 1.0 g (3.8 mmol) of (5β,8β)-9,10-didehydro-6-methylergoline-8-acetonitrile was stirred overnight and gave 0.37 g of the title compound (37%) after recrystallization from a mixture of ethyl acetate/diethyl ether, mp. 180°-182° C., [α]589nm +14° (c=0.46 percent, pyridine).

Sources & evidence

ORD record
ord-7a8e7467f9894b09bfeddb9c1351d3ad
Source dataset
uspto-grants-1989_01
Patent number
US04798834

Reaction notes

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