Erythromycin → (9S)-9-Dihydroerythromycin A

HRID 1348556Notes

Reaction equation

HRID 1348556 reaction equation
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].[BH4-].[Na+]>C1COCC1>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C@H:7]([OH:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

Participants

4

Reactant 2

HCID 12560ErythromycinHCID 4311764Sodium borohydride

Product 1

HCID 13132032(9S)-9-Dihydroerythromycin AYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of erythromycin A (22.0 g, 30 mmol) in THF (200 mL) cooled to −10° C. was added NaBH4 (2.27 g, 60 mmol) in small portions. The mixture was then allowed to stir at 0° C. for 3 h before the reaction was quenched with water. After evaporation of the majority of the solvent, dilute NaHCO3 solution was added, the mixture was extracted three times with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4. The crude product was purified by silica gel chromatography using 2:1 hexane-acetone with 1% Et3N to give pure product (12.8 g, 58% yield). m/z: 736.5 (MH); 13C-NMR (CDCl3): 177.00, 103.21, 96.32, 84.20, 83.10, 79.23, 77.72, 77.63, 74.99, 74.48, 72.66, 70.75, 70.69, 69.29, 66.09, 65.02, 49.32, 45.52, 41.73, 40.32 (2×), 36.91, 34.84, 34.23, 31.97, 28.81, 25.25, 21.68, 21.51, 21.18, 20.06, 18.12, 16.50, 15.06, 14.80, 10.81, 9.36.

Workup

  1. customwas quenched with water
  2. customAfter evaporation of the majority of the solvent, dilute NaHCO3 solution
  3. additionwas added
  4. extractionthe mixture was extracted three times with EtOAc
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a8e7b5bcc1c24025ae3c1b39599ac2cd
Source dataset
uspto-grants-2007_05
Patent number
US07211568B2

Reaction notes

Loading…