Triethylsilane → HCID 14107790, compound

HRID 2291825Notes

Reaction equation

HRID 2291825 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][S:26][CH3:27])[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][S:26][CH3:27])[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][S:26][CH3:27])[CH2:10]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 14107771HCID 14107771, compound

Product 2

HCID 14107771HCID 14107771, compoundHCID 14107790HCID 14107790, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(5β,8β)-9,10-didehydro-6-methyl-8-(methylthiomethyl)ergoline was prepared according to the method of Kornfeld et al. in U.S. Pat. No. 3,901,894. Following procedures essentially as described in Example 1, a mixture of 20 ml of TFA, 5.24 g (45.1 mmol) of triethylsilane and 3.1 g (10.9 mmol) of (5β,8β)-9,10-didehydro-6-methyl-8-(methylthiomethyl)ergoline was stirred for 5 hours and gave 1.34 g of the title compound (42%) after HPLC and recrystallization from a mixture of diethyl ether/hexane, mp. 93°-97° C.

Sources & evidence

ORD record
ord-50bd1fae80714eceaecbbdae9b314494
Source dataset
uspto-grants-1989_01
Patent number
US04798834

Reaction notes

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