Butanal → Budesonide

HRID 2309487Notes

Reaction equation

HRID 2309487 reaction equation
[CH3:1][C@@:2]12[C@:10]3([C:16]([CH2:18][OH:19])=[O:17])[O:11][C:12]([CH3:15])(C)[O:13][C@@H:9]3[CH2:8][C@H:7]1[C@@H:6]1[CH2:20][CH2:21][C:22]3[C@@:28]([CH3:29])([C@H:5]1[C@@H:4]([OH:30])[CH2:3]2)[CH:27]=[CH:26][C:24](=[O:25])[CH:23]=3.[CH:31](=O)[CH2:32]CC.F>O>[CH3:31][CH2:32][CH2:15][CH:12]1[O:11][C@:10]2([C:16]([CH2:18][OH:19])=[O:17])[C@@H:9]([CH2:8][C@@H:7]3[C@:2]2([CH3:1])[CH2:3][C@H:4]([OH:30])[C@H:5]2[C@H:6]3[CH2:20][CH2:21][C:22]3[C@:28]2([CH3:29])[CH:27]=[CH:26][C:24](=[O:25])[CH:23]=3)[O:13]1

Participants

5

Reactant 3

HCID 261ButanalHCID 14917Hydrofluoric AcidHCID 5311066Desonide

Product 1

HCID 5281004Budesonide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

50 Grams of desonide (16α-hydroxyprednisolone-16,17-acetonide) and immediately thereafter 12,5 ml of butyraldehyde were added to 500 ml of a 70% hydrofluoric acid solution, at -5° C. The mixture was stirred at 0° C. for one hour and then poured into 5 liters of demineralized water at 0° C. The precipitate was filtered, washed to neutrality with water and dried under vacuum to give 51 g of pure budesonide with an A/B epimer ratio of 9/91.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d35f1504ede64ea6bbf911b84fab18fe
Source dataset
uspto-grants-1987_09
Patent number
US04695625

Reaction notes

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