Sodium Bicarbonate → HCID 53723341, compound

HRID 1604105Notes

Reaction equation

HRID 1604105 reaction equation
[OH:1][CH2:2][CH:3]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[C:13]([N+:25]([O-])=O)[C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)[CH3:4].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:25][C:13]1[C:14](=[O:24])[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12]=1[CH2:11][CH2:10][C@@H:9]1[C@@H:19]2[CH2:20][CH2:21][C@@:22]2([CH3:23])[C@H:8]1[CH2:7][CH2:6][C@@H:5]2[CH:3]([CH2:2][OH:1])[CH3:4]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 54157668HCID 54157668, compound

Product 1

HCID 53723341HCID 53723341, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 20-hydroxymethyl-4-nitropregn-4-en-3-one (0.52 g, 1.38 ml) in absolute ethanol (4.8 mL) is combined with stannous chloride (2.1 g) added in one portion and then heated to 70° C. for 6 hours. The reaction vessel is then cooled to room temperature and the solution is carefully neutralized with sodium bicarbonate (9 g) over a 10 minute period. The resulting slurry is then filtered, removing a brown solid which is then stirred in 10% hydrofluoric acid (25 mL) and ethyl acetate (25 mL). The HF/EtOAc treatment is repeated. The organic phases from each filtration are combined, dried over magnesium sulphate, filtered and concentrated. The resulting residue is purified by flash chromatagraphy to give 4-amino-20-hydroxymethylpregn-4-en-3-one as a white solid identical to the material described in U.S. Pat. No. 5,218,110 to Weintraub and U.S. Pat. No. 5,120,840 to Weintraub et al., which are both herein incorporated by reference. The compound has the following formula: ##STR35##

Workup

  1. additionadded in one portion
  2. temperatureThe reaction vessel is then cooled to room temperature
  3. filtrationThe resulting slurry is then filtered
  4. customremoving a brown solid which
  5. filtrationThe organic phases from each filtration
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by flash chromatagraphy

Sources & evidence

ORD record
ord-3f2163e19cb04f20a095fd1fee6501b9
Source dataset
uspto-grants-1999_11
Patent number
US05990328

Reaction notes

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