Hydrochloric Acid → 3-(Benzyloxy)pyrrolidine

HRID 1045683Notes

Reaction equation

HRID 1045683 reaction equation
Cl.[CH2:2]([O:9][CH:10]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C.C(OCC)C>[CH2:2]([O:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57870122HCID 57870122, compound

Product 1

HCID 144973533-(Benzyloxy)pyrrolidineYield 40.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride (4N) in ethyl acetate (1.5 ml) was added to a solution of crude 3-benzyloxy-1-(tert-butoxycarbonyl)-pyrrolidine (705 mg) in diethyl ether (3 ml) and the mixture was stirred for 15 minutes. Reaction was quenched with water, and the solution was washed with diethyl ether. After addition of aqueous sodium hydroxide to make the solution basic, the solution was extracted with diethyl ether and the organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure afforded 3-benzyloxy-pyrrolidine (182 mg, 37%).

Workup

  1. customReaction
  2. customwas quenched with water
  3. washthe solution was washed with diethyl ether
  4. additionAfter addition of aqueous sodium hydroxide
  5. extractionthe solution was extracted with diethyl ether
  6. washthe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c595ea4b76784d8d85caba06cd5c2bd7
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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