Sodium borohydride → HCID 121396372, compound

HRID 60713Notes

Reaction equation

HRID 60713 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]2[O:7][C@H:8]([C:10](=[O:14])[CH2:11][O:12][CH3:13])[CH2:9][C@H:4]2[O:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]([OH:14])[CH2:11][O:12][CH3:13])[CH2:9][C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1213963641-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanone2×

Product 1

HCID 121396372HCID 121396372, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanone (compound 21c, 1.4 g, 6.5 mmol) in methanol (50 mL) was added sodium borohydride (494 mg, 13 mmol). After being stirred at room temperature for 2 hours, the resulting solution was quenched by saturated NH4Cl solution and concentrated in vacuo. The residue was suspended in EtOAc and then filtered. The filtrate was concentrated in vacuo to afford 1.24 g of crude product of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanol (compound 21d) as a colorless oil. MS obsd. (ESI+) [(M+NH4)+]: 236.

Workup

  1. customthe resulting solution was quenched by saturated NH4Cl solution
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3aa14fa52d194a5598618a4e5d21a851
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…