Trifluoroacetic acid → HCID 14107796, compound

HRID 2291827Notes

Reaction equation

HRID 2291827 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C:28]([CH2:29]2)=[CH:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:17]1>>[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C:28]([CH2:29]2)=[CH:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:17]1.[CH3:15][N:16]1[C@H:30]2[C:20]([C:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:31]=3[C@H:28]([CH2:29]2)[CH2:27][NH:26]4)=[CH:19][C@@H:18]([CH2:32][S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14107774HCID 14107774, compound

Product 2

HCID 14107774HCID 14107774, compoundHCID 14107796HCID 14107796, compoundYield 69.4%

Procedure

(5β,8β)-9,10-didehydro-6-methyl-8-(phenylthiomethyl)ergoline was prepared as described by Kornfeld et al. supra. Following procedures essentially as described in Example 1, a mixture of 12 ml of TFA, 3.0 g (26.1 mmol) of triethylsilane and 2.32 g (6.7 mmol) of (5β,8β)-9,10-didehydro-6-methyl-8-(phenylthiomethyl)ergoline was stirred overnight and provided 0.81 g of the title compound (35%) following HPLC (5% methanol/methylene chloride), mp. 54°-58° C.

Sources & evidence

ORD record
ord-4fa8006b98764f64a8071b6e0685892e
Source dataset
uspto-grants-1989_01
Patent number
US04798834

Reaction notes

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