Hydrochloric Acid → HCID 86707547, compound

HRID 339070Notes

Reaction equation

HRID 339070 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@H:16]([O:17][CH3:18])[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:18][O:17][C@@H:16]1[CH2:15][NH:14][CH2:13][C@H:12]1[NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70982902HCID 70982902, compound

Product 1

HCID 86707547HCID 86707547, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-methoxypyrrolidine-1-carboxylate (2.90 g, 8.28 mmol) in DCM (20 mL) was added 4 N HCl (20.69 mL, 82.76 mmol) in dioxane. The reaction mixture was stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure. Saturated bicarbonate (20 mL) and DCM (50 mL) were added. The organic layer was separated, dried (sodium sulfate), filtered and concentrated under reduced pressure to give benzyl (3R,4R)-4-methoxypyrrolidin-3-ylcarbamate (2.0 g, 96.6%) as oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionSaturated bicarbonate (20 mL) and DCM (50 mL) were added
  3. customThe organic layer was separated
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f6ef1658b2c4aa687df57fa280cf22a
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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