2-Benzylhexahydropyrano[3,4-c]pyrrol-4(1H)-one → HCID 86729486, compound

HRID 712441Notes

Reaction equation

HRID 712441 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]2[CH2:13][CH2:14][O:15][C:16](=[O:17])[CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH:10]([CH2:16][OH:17])[CH:11]([CH2:13][CH2:14][OH:15])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 34744972-Benzylhexahydropyrano[3,4-c]pyrrol-4(1H)-oneHCID 4148881Lithium borohydride

Product 1

HCID 86729486HCID 86729486, compoundYield 80.62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzylhexahydropyrano[3,4-c]pyrrol-4(2H)-one (2.82 g) in THF (70 mL) was added LiBH4 (0.40 g) at 0° C. under N2. The reaction mixture was stirred for 7 h at room temperature and concentrated in vacuo. The residue was dissolved in MeOH (50 mL) and heated to reflux for 16 h. The mixture was concentrated in vacuo and redissolved in EtOAc (100 mL), then washed with water followed by brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound (2.31 g, 80.62%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 236.3 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH (50 mL)
  3. temperatureheated
  4. temperatureto reflux for 16 h
  5. concentrationThe mixture was concentrated in vacuo
  6. dissolutionredissolved in EtOAc (100 mL)
  7. washwashed with water
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35ae35f602a542009763801d194747f9
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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