Sodium borohydride → HCID 70981793, compound

HRID 2280699Notes

Reaction equation

HRID 2280699 reaction equation
[O:1]=[C:2]1[CH2:7][O:6][CH2:5][CH:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][O:6][CH2:5][CH:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 25260225benzyl 5-oxotetrahydro-2H-pyran-3-ylcarbamate

Product 1

HCID 70981793HCID 70981793, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl 5-oxotetrahydro-2H-pyran-3-ylcarbamate (4.35 g, 17.45 mmol) and cerium(III) chloride heptahydrate (6.50 g, 17.45 mmol) were dissolved in methanol (100 mL) before cooling to 0° C. Sodium borohydride (0.660 g, 17.45 mmol) was then added slowly. Intense bubbling was observed. The reaction was allowed to stir at 0° C. for 30 min before quenching by addition of acetone (˜3 mL) and stirring at room temperature for 30 additional min. The reaction was then evaporated to dryness. The material was partitioned between DCM and water and the aqueous layer was washed with DCM (5×). The organic layers were combined, dried over sodium sulfate, filtered, and condensed to give impure benzyl 5-hydroxytetrahydro-2H-pyran-3-ylcarbamate (2.5 g, 9.95 mmol, 57.0% yield) as a white solid; 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.39 (m, 5H), 5.90-6.06 (m, 1H), 5.10 (d, J=4.29 Hz, 2H), 3.59-3.97 (m, 6H), 1.77-2.06 (m, 3H; MS (ESI) m/z 252.1 [M+1]+.

Workup

  1. customIntense bubbling
  2. custombefore quenching by addition of acetone (˜3 mL)
  3. stirringstirring at room temperature for 30 additional min
  4. customThe reaction was then evaporated to dryness
  5. customThe material was partitioned between DCM and water
  6. washthe aqueous layer was washed with DCM (5×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customcondensed

Sources & evidence

ORD record
ord-3d73b386a90148a8aa8a60a6b0e30a52
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…