Water → HCID 11439824, compound

HRID 1675907Notes

Reaction equation

HRID 1675907 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C=O)C>[CH2:23]([O:20][C:9]1[CH:8]=[CH:7][C:6]2[CH:5]3[CH:14]([CH2:13][CH2:12][C:11]=2[CH:10]=1)[CH:15]1[C:2]([CH3:1])([C:18](=[O:19])[CH2:17][CH2:16]1)[CH2:3][CH2:4]3)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5870EstroneHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 11439824HCID 11439824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 15 g (55 mmol) of estrone in DMF (110 mL) was cooled to 0° C. and 2.44 g (61 mmol) of NaH (60% in oil) were added slowly. The mixture was stirred at 0° C. under N2 for 1 h before addition of 13.2 mL (111 mmol) of benzyl bromine dropwise at 0° C. The reaction was then heated to 80° C. for 4 h. After cooling, the mixture was poured into water. The suspension was extracted by diethyl ether (5 times). The mixed organic layer were washed with 2N HCl (3 times) and brine, dried over Na2SO4 and concentrated in vacuo. Recrystallisation of the solid residue in ethanol gave 12.33 g (62%) of JAC01002 as beige solid. 1H NMR (400 MHz, CDCl3) δ 0.92 (s, 3H, CH3); 1.49-1.63 (m, 6H); 1.99-2.05 (m, 3H); 2.17 (dAB, J=18.9, 8.9 Hz, 1H); 2.23 (m, 1H); 2.40 (m, 1H); 2.51 (dAB, J=18.9, 8.9, 1H); 2.85 (m, 2H, CH26); 5.05 (s, 2H, OH2Ph); 6.74 (d, J=2.8 Hz, 1H, H4); 6.80 (dd, J=8.5, 2.8 Hz, 1H, H2); 7.21 (d, J=8.5 Hz, 1H, H1); 7.30-7.45 (m, 5H); Acq. Mass (FAB+) calcd 360.2089, obsd 360.21675 (M+).

Workup

  1. temperatureAfter cooling
  2. extractionThe suspension was extracted by diethyl ether (5 times)
  3. washThe mixed organic layer were washed with 2N HCl (3 times) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customRecrystallisation of the solid residue in ethanol
  7. customgave 12.33 g (62%) of JAC01002 as beige solid

Sources & evidence

ORD record
ord-12249120a57b425ca7a48a15ae2850af
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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