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

HRID 272097Notes

Reaction equation

HRID 272097 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-607e516fc46f44798928a6187dc4c104
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

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