Trifluoroacetic acid → Ethyl (3S,4R)-4-amino-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate

HRID 655755Notes

Reaction equation

HRID 655755 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@@H:10]1[O:20][CH2:21][CH:22]=[CH2:23])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@@H:10]1[O:20][CH2:21][CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58074870Ethyl (3S,4R)-4-[(tert-butoxycarbonyl)amino}-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate2×

Product 1

HCID 58075108Ethyl (3S,4R)-4-amino-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (3S,4R)-4-[(tert-butoxycarbonyl)amino}-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate (Intermediate 17, 5 g, 12.7 mmol) was dissolved in dichloromethane (200 mL) and trifluoroacetic acid (9.79 mL, 127 mmol) was added. The reaction mixture was allowed to stir for 3 h at room temperature. The reaction mixture was basified with saturated sodium bicarbonate solution (pH ˜8) and the layers were separated. The aqueous layer was extracted with dichloromethane; organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 2.7 g (93.24%). MS (ES) (M+H): 228. for C11H20N2O3.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialorganic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto afford 2.7 g (93.24%)

Sources & evidence

ORD record
ord-a63b706b24b9418c911911c529465a05
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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