Estrone → HCID 4017561, compound

HRID 1675915Notes

Reaction equation

HRID 1675915 reaction equation
[OH-].[Na+].[CH3:3][C@@:4]12[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C@H:16]1[C@@H:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:22])=[CH:12][C:13]=3[CH2:14][CH2:15]1)[CH2:6][CH2:5]2.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>C(O)C>[OH:22][C:11]1[CH:10]=[CH:9][C:8]2[CH:7]3[CH:16]([CH2:15][CH2:14][C:13]=2[CH:12]=1)[CH:17]1[C:4]([CH3:3])([C:20](=[O:21])[C:19](=[CH:29][C:26]2[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=2)[CH2:18]1)[CH2:5][CH2:6]3

Participants

6

Reactant 4

HCID 5870EstroneHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 4017561HCID 4017561, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1.0 g, 25 mmol) was added to a suspension of estrone (1.35 g, 5.0 mmol) and pyridine-4-carbaldehyde (595 mg, 5.0 mmol) in ethanol (40 mL) at room temperature. The resulting dark orange solution was stirred at room temperature for 4 hours. Then glacial acetic (ca. 10 mL) acid was added with stirring. The colour changed to light yellow and a light yellow solid precipitated. The solid was filtered off and washed with water (50 mL), ethanol (20 mL), diethyl ether (50 mL) and hexane (50 mL) and dried under high vacuum. Yield: 1.588 g (88%) light yellow solid. 1H-NMR (DMSO-d6, 400 MHz), δ: 0.92 (s, 3H, —CH3), 1.30-1.68 (m, 5H), 1.82-1.92 (m, 1H), 1.96-2.04 (m, 1H), 2.14-2.24 (m, 1H), 2.31-2.38 (m, 1H), 2.61-2.69 (m, 1H), 2.71-2.84 (m, 2H), 2.87-2.96 (m, 1H), 6.47 (d, J=2.3 Hz, 1H), 6.53 (dd, J=8.6, 2.3 Hz, 1H), 7.06 (d, J=8.6 Hz, 1H), 7.28 (s, 1H), 7.60 (d, J=6.2 Hz, 2H), 8.65 (d, J=6.2 Hz, 2H), 9.05 (s, 1H, —OH). LRMS (FAB+): 360.2 (100, [M+H]+). LRMS (FAB−): 358.2 (100, [M−H]−). HRMS (FAB+): 360.196986 C24H26NO2 requires 360.196354.

Workup

  1. stirringwith stirring
  2. customprecipitated
  3. filtrationThe solid was filtered off
  4. washwashed with water (50 mL), ethanol (20 mL), diethyl ether (50 mL) and hexane (50 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-066a51aad5884958974aa1e222e47e9d
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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