Ethylamine → HCID 12962025, compound

HRID 1065712Notes

Reaction equation

HRID 1065712 reaction equation
C(O)(=O)C.C(O)(=O)C.[OH:9][C:10]1[CH:27]=[CH:26][C:25]2[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=O)[C@H:18]([OH:29])[CH2:17]4)[CH2:14][CH2:13][C:12]=2[CH:11]=1.[CH2:30]([NH2:32])[CH3:31].[BH4-].[Na+].C(=O)(O)[O-].[K+].[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44]>CS(C)=O>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44].[CH2:30]([NH:32][C@H:19]1[C@H:18]([OH:29])[CH2:17][C@H:16]2[C@H:15]3[C@H:24]([CH2:23][CH2:22][C@:20]12[CH3:21])[C:25]1[CH:26]=[CH:27][C:10]([OH:9])=[CH:11][C:12]=1[CH2:13][CH2:14]3)[CH3:31]

Participants

7

Reactant 5

HCID 6341EthylamineHCID 444266Maleic AcidHCID 516893Potassium BicarbonateHCID 4311764Sodium borohydrideHCID 86738380HCID 86738380, compound

Product 1

HCID 12962025HCID 12962025, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a similar way as described in Example XXI 3,16α-dihydroxy-oestra-1,3,5(10)-trien-17-one diacetate was converted with ethylamine into the intermediate 17-ethylimine, which was reduced with sodium borohydride. Hydrolysis with potassium bicarbonate, followed by treatment with maleic acid gave the title compound, m.p. 147° C. (decomp.), [α]D +32.9° (c 1.07 in dimethylsulphoxide).

Sources & evidence

ORD record
ord-5ae8baa4dcda4f4a9b91b561a3ed1ab8
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

Loading…