Hydrochloric Acid → tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylate

HRID 394049Notes

Reaction equation

HRID 394049 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>O1CCCC1>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 10083012(S)-Tert-butyl 3-(azidomethyl)piperidine-1-carboxylate

Product 1

HCID 1502023tert-Butyl (3R)-3-(aminomethyl)piperidine-1-carboxylateYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 600 mg of (3S)-3-azidomethyl-1-(tert-butoxycarbonyl)piperidine in 12.5 ml of 20% hydrous tetrahydrofuran, 622 mg of triphenylphosphine was added at room temperature, followed by 45 minutes' refluxing under heating. The reaction liquid was rendered acidic by addition of 0.5 N hydrochloric acid, and successively washed with chloroform and ethyl acetate. Then 4N aqueous sodium hydroxide solution was added to the aqueous layer to render the latter basic, followed by extraction with chloroform and drying over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 497 mg of the title compound was obtained.

Workup

  1. temperature' refluxing
  2. temperatureunder heating
  3. customThe reaction liquid
  4. washsuccessively washed with chloroform and ethyl acetate
  5. additionThen 4N aqueous sodium hydroxide solution was added to the aqueous layer
  6. extractionfollowed by extraction with chloroform
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-963f4bc1c8c8429fb5a34c9a88126b4a
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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