Tetrahydrofuran → HCID 18633454, compound

HRID 232379Notes

Reaction equation

HRID 232379 reaction equation
[BH4-].[Li+].[C:3]([O:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=O)[O:10][C@@H:9]([N:19]2[CH:26]=[C:25]([CH2:27][CH3:28])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:8]1)(=[O:5])[CH3:4].[O:29]1CCCC1>>[C:17]([O:16][CH2:14][CH2:13][CH2:12][C@H:11]1[O:10][C@@H:9]([N:19]2[CH:26]=[C:25]([CH2:27][CH3:28])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:8][C@@H:7]1[O:6][C:3](=[O:5])[CH3:4])(=[O:29])[CH3:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride2×HCID 18633448HCID 18633448, compound

Product 1

HCID 18633454HCID 18633454, compound

Procedure

0.4 g of lithium borohydride was added to a solution of 5.6 g of 3'-O-acetyl-2',5'-dideoxy-5'-(ethoxycarbonylmethyl)-5-ethyluridine in 100 ml of tetrahydrofuran and the mixture was stirred at room temperature for 4 hours. An additional 0.2 g of lithium borohydride was added and the mixture was stirred at room temperature overnight and then heated under reflux for 1 hour. The solvent was removed by evaporation in vacuo and the residue was dissolved in methanol. After standing at room temperature for a few minutes, the solvent was removed by evaporation and the residue was taken up in 40 ml of pyridine. 5 g of acetic anhydride were added and the mixture was stirred at room temperature overnight. Pyridine was removed by evaporation and the residue was partitioned between water and ethyl acetate. The aqueous solution was evaporated to dryness and the residue was subjected to flash chromatography on a column of silica gel using 10% methanol/dichloromethane for the elution to give 1.3 g of 5'-(2-acetoxyethyl)- 3'-O-acetyl-2',5'-dideoxy-5-ethyluridine in the form of a colorless oil which crystallized upon standing.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. customThe solvent was removed by evaporation in vacuo
  5. dissolutionthe residue was dissolved in methanol
  6. waitAfter standing at room temperature for a few minutes
  7. customthe solvent was removed by evaporation
  8. addition5 g of acetic anhydride were added
  9. stirringthe mixture was stirred at room temperature overnight
  10. customPyridine was removed by evaporation
  11. customthe residue was partitioned between water and ethyl acetate
  12. customThe aqueous solution was evaporated to dryness
  13. washthe residue was subjected to flash chromatography on a column of silica gel using 10% methanol/dichloromethane for the elution

Sources & evidence

ORD record
ord-db6499cc1d6742ebb3e733d3fe71fa3d
Source dataset
uspto-grants-1989_07
Patent number
US04851519

Reaction notes

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