Sodium borohydride → HCID 86714092, compound

HRID 2206747Notes

Reaction equation

HRID 2206747 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C@@H:10]2[O:17][C@@H:16]3[C@@H:12]([O:13][C:14]([CH3:19])([CH3:18])[O:15]3)[C@@H:11]2[OH:20])=[O:9])=[CH:4][C:3]=1[CH2:21][C:22]1[CH:31]=[CH:30][C:25]2[O:26][CH2:27][CH2:28][O:29][C:24]=2[CH:23]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:9])[C@@H:10]2[O:17][C@@H:16]3[C@@H:12]([O:13][C:14]([CH3:18])([CH3:19])[O:15]3)[C@@H:11]2[OH:20])=[CH:4][C:3]=1[CH2:21][C:22]1[CH:31]=[CH:30][C:25]2[O:26][CH2:27][CH2:28][O:29][C:24]=2[CH:23]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71110772HCID 71110772, compound

Product 1

HCID 86714092HCID 86714092, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 135 (0.77 g, 1.7 mmol) in CH3OH was added CeCl3−7H2O and the mixture was stirred at room temperature until all solids were dissolved. The mixture was then cooled to −78° C. and NaBH4 was added in portions. The mixture was stirred for 1 h at −78° C., slowly warmed to 0° C. and quenched with saturated NH4Cl solution. The mixture was concentrated under reduced pressure to remove CH3OH and then extracted with EtOAc and washed with saturated NaCl solution. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the desired alcohol (0.67 g, 87%) as a white solid. The obtained product was used for the next step without purification.

Workup

  1. dissolutionwere dissolved
  2. temperatureThe mixture was then cooled to −78° C.
  3. stirringThe mixture was stirred for 1 h at −78° C.
  4. temperatureslowly warmed to 0° C.
  5. customquenched with saturated NH4Cl solution
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customto remove CH3OH
  8. extractionextracted with EtOAc
  9. washwashed with saturated NaCl solution
  10. dry with materialThe organic layer was dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40f75ae2251b4f72a9b28f52976c5ff3
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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