p-Toluenesulfonic acid → HCID 13935078, compound

HRID 231208Notes

Reaction equation

[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20]([OH:22])=[O:21])[CH2:10][NH:9]4)=[CH:5]1)([CH3:3])[CH3:2].[CH:23]1(O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:21])[CH2:10][NH:9]4)=[CH:5]1)([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6101p-Toluenesulfonic acid

HCID 7966Cyclohexanol

HCID 13806529HCID 13806529, compound

Product 1

HCID 13935078HCID 13935078, compound

Procedure

Following the procedure of Example 1, 1.5 g of 1-isopropylergoline-8β-carboxylic acid were esterified with 15 g of cyclohexanol in the presence of 1.5 g of p-toluenesulfonic acid to yield 1-isopropyl-8β-(cyclohexyloxycarbonyl)ergoline. The product, 1.91 g of an oil, was converted to the maleate salt in a 6:1 ether/ethyl acetate solvent mixture. The salt was isolated by evaporation and then recrystallized from ether/methanol; yield=0.93 g of cyclohexyl 1-isopropyl-8β-(cyclohexyloxycarbonyl)ergoline maleate (96.77% pure by HPLC); molecular ion at 380; [α]25D =-40.64° .

Sources & evidence

ORD record: ord-5eeb9bdef456485d8872d7b0efc030e6
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845224

Reaction notes

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