Hydrochloric Acid → tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

HRID 2206524Notes

Reaction equation

HRID 2206524 reaction equation
CC(C)([S@@]([NH:6][C@H:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)[CH3:8])=O)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>CO>[NH2:6][CH:7]([CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:13][CH2:14]1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 117779509tert-butyl 4-((S)-1-((S)-1,1-dimethylethylsulfinamido)ethyl)piperidine-1-carboxylate

Product 1

HCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateYield 110.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1 L round bottomed flask charged with a magnetic stir bar was added crude tert-butyl 4-((S)-1-((S)-1,1-dimethylethylsulfinamido)ethyl)piperidine-1-carboxylate (29 g) was taken up in MeOH (200 mL) before addition of a 4 N solution of HCl in 1,4-dioxane (24.06 ml, 96 mmol). The resulting solution was then stirred at room temperature for 1H at rt. The methanol was then removed in vacuo to afford viscous oil which was treated with sat'd aqueous NaHCO3 (˜500 mL) and extracted with ethyl acetate (2×500 mL). This organic phase was combined, dried with MgSO4, filtered, and solvent was then removed in vacuo affording the title compound (22 g) which was used without further purification.

Workup

  1. additionTo a 1 L round bottomed flask charged with a magnetic stir bar
  2. customThe methanol was then removed in vacuo
  3. customto afford viscous oil which
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customsolvent was then removed in vacuo

Sources & evidence

ORD record
ord-e8ea8b568d8645fd957efe6907e99471
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…