Trifluoroacetic acid → HCID 14107782, compound

HRID 2291824Notes

Reaction equation

HRID 2291824 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.[OH:15][CH2:16][C@@H:17]1[CH:32]=[C:31]2[C@@H:21]([CH2:22][C:23]3[C:33]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]2=4)[NH:25][CH:24]=3)[N:19]([CH3:20])[CH2:18]1>>[OH:15][CH2:16][C@@H:17]1[CH:32]=[C:31]2[C@@H:21]([CH2:22][C:23]3[C:33]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]2=4)[NH:25][CH:24]=3)[N:19]([CH3:20])[CH2:18]1.[OH:15][CH2:16][C@@H:17]1[CH:32]=[C:31]2[C@@H:21]([CH2:22][C@H:23]3[C:33]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]2=4)[NH:25][CH2:24]3)[N:19]([CH3:20])[CH2:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 149871413-67-8

Product 2

HCID 149871413-67-8HCID 14107782HCID 14107782, compoundYield 50.7%

Procedure

Lysergol was prepared as described by Stoll et al., Helv. Chim. Acta 1949, 32, 1949. Following procedures essentially as described in Example 1, a mixture of 7 ml of TFA, 1.78 g (15.28 mmol) triethylsilane and 0.508 g (2.0 mmol) of lysergol was stirred for 3 hours and gave 0.13 g of the title compound (25%) following column chromatography (50 g silica gel, chloroform:methanol: ammonium hydroxide eluent, 8:2:0.5%), mp. 177°-178.5° C.

Sources & evidence

ORD record
ord-eebfcca771234d88a030883c5372d46a
Source dataset
uspto-grants-1989_01
Patent number
US04798834

Reaction notes

Loading…