Methanol → HCID 60128538, compound

HRID 877710Notes

Reaction equation

HRID 877710 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2]2.S(=O)(=O)(O)O.[CH3:22][OH:23]>>[OH:23][C@H:22]1[C@H:1]([O:6][CH3:5])[CH2:2][N:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 60128538HCID 60128538, compoundYield 69.8%

Procedure

Benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (21.0 g, 96 mmol) was dissolved in MeOH (200 mL). Added sulfuric acid (3.64 g, 37.1 mmol) dropwise. After ˜3 hrs the reaction was concentrated and the residue was diluted with ethyl acetate and neutralized with 1N aq. NaOH. The organic extract was dried (Na2SO4) and concentrated. The reaction product was purified by silica gel column chromatography eluting with Hexane/Acetone mixtures to give (+/−)-Trans-benzyl 3-hydroxy-4-methoxypyrrolidine-1-carboxylate (16.8 g, 66.9 mmol, 69.8% yield) LCMS:M+1=252, Rt=1.42 min.

Workup

  1. concentrationAfter ˜3 hrs the reaction was concentrated
  2. additionthe residue was diluted with ethyl acetate and neutralized with 1N aq. NaOH
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe reaction product was purified by silica gel column chromatography
  7. washeluting with Hexane/Acetone

Sources & evidence

ORD record
ord-275021ba646642378b46d6b6cff31d21
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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