Hydrochloric Acid → (R)-1-Cbz-3-aminopiperidine

HRID 1685185Notes

Reaction equation

HRID 1685185 reaction equation
Cl.[CH2:2]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:18]C(OC(C)(C)C)=O)[CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1.C(Cl)Cl.CO>[CH2:2]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([NH2:18])[CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 50999064(R)-3-N-Boc-Amino-1-Cbz-piperidine

Product 1

HCID 1514177(R)-1-Cbz-3-aminopiperidineYield 104%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4M HCl in dioxane (100 mL) to a solution of (R)-3-tert-butoxycarbonylamino-piperidine-1-carboxylic acid benzyl ester (71.65 mmol; 23.96 g) in DCM (100 mL) and MeOH (10 mL). Stir 60 min and evaporate. Partition solid between DCM and saturated sodium bicarbonate aqueous, extract three times with DCM, Wash extracts with brine, dry over MgSO4, filter through Celite® and evaporate to give the title compound 17.39 g (74.22 mmol; 104%). MS (ES+): m/z=235 (M+H).

Workup

  1. customevaporate
  2. customPartition solid between DCM and saturated sodium bicarbonate aqueous
  3. extractionextract three times with DCM
  4. washWash
  5. dry with materialdry over MgSO4
  6. filtrationfilter through Celite®
  7. customevaporate

Sources & evidence

ORD record
ord-35475421bac0412c853e0d81d28995e1
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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