Water → HCID 86635554, compound

HRID 42074Notes

Reaction equation

HRID 42074 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:7][CH2:6][CH:5]([O:8][NH2:9])[CH2:4]1.[CH3:10][C@:11]12[CH2:28][CH2:27][C@H:26]3[C@@H:16]([CH2:17][C:18](=[O:30])[CH:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][C:21](=O)[CH2:20]4)[C@@H:15]1[CH2:14][CH2:13][C:12]2=[O:31].O.[Na+].[Cl-]>C1COCC1>[ClH:1].[NH:3]1[CH2:7][CH2:6][CH:5]([O:8][N:9]=[C:21]2[CH2:22][CH2:23][C@@:24]3([CH3:25])[CH:19]([C:18](=[O:30])[CH2:17][C@@H:16]4[C@@H:26]3[CH2:27][CH2:28][C@@:11]3([CH3:10])[C@H:15]4[CH2:14][CH2:13][C:12]3=[O:31])[CH2:20]2)[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 54071530Androstane-3,6,17-trioneHCID 68786623HCID 68786623, compound

Product 1

HCID 86635554HCID 86635554, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(RS)-pyrrolidinyloxyamine dihydrochloride (III-c, Prepn. 3, 227 mg) and androstane-3,6,17-trione (495 mg) in THF: water (2/1, 27 mL) was stirred for 30 min. NaCl was added and stirred till the two phases separated. After extraction of the aqueous layer with THF, the combined organic phases were washed with brine, dried and evaporated. The crude was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3 9:1:0.1). To the concentrated fractions 5M HCl in EtOAc was added. After dilution with Et2O, the solid was collected by filtration to give the title compound I-ac (464 mg, 60%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 9.59 (1H, bb), 9.41 (1H, bb), 4.74 (1H, m), 3.80-2.90 (5H, m), 2.60-1.20 (21H, m), 0.78 (6H, s).

Workup

  1. customseparated
  2. extractionAfter extraction of the aqueous layer with THF
  3. washthe combined organic phases were washed with brine
  4. customdried
  5. customevaporated
  6. customThe crude was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3 9:1:0.1)
  7. additionTo the concentrated fractions 5M HCl in EtOAc was added
  8. filtrationAfter dilution with Et2O, the solid was collected by filtration

Sources & evidence

ORD record
ord-b12edf065d154ea58493525b0a357ce4
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

Loading…