Methylamine → HCID 22941792, compound

HRID 650338Notes

Reaction equation

HRID 650338 reaction equation
[CH3:1][NH2:2].[C:3]([O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:17][C:16]=1[CH2:15][C@H:14]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:5])[CH3:4]>O1CCCC1>[C:3]([O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:17][C:16]=1[CH2:15][C@H:14]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:2][CH3:1])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22941787HCID 22941787, compound

Product 1

HCID 22941792HCID 22941792, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.3 g of methylamine is condensed in a pressure pipe while being cooled with ice in a solution of 8.2 g of 17β-acetoxy-3-(tetrahydropyran-2-yloxy)-7α-(5-p-toluenesulfonyloxypentyl)-estra-1,3,5(10)-triene in 80 ml of tetrahydrofuran. The closed pressure pipe is then heated for 6 hours to 60° C. After cooling, it is evaporated to dryness in a vacuum, and the residue is chromatographed on silica gel. 5.1 g of 17β-acetoxy-7α-(5-methylaminopentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene is obtained as oil. [α]D22=+29.7°(c=0.535% in chloroform)

Workup

  1. customcondensed in a pressure pipe
  2. temperatureThe closed pressure pipe is then heated for 6 hours to 60° C
  3. temperatureAfter cooling
  4. customit is evaporated to dryness in a vacuum
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-7ae3ee0fee744b429c992b6e4016b077
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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