Hydrochloric Acid → (S)-Benzyl 2-(3-amino-2-oxopiperidin-1-yl)acetate hydrochloride

HRID 1636512Notes

Reaction equation

HRID 1636512 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:10]1=[O:26])=O)(C)(C)C.[ClH:27]>C(OCC)(=O)C>[ClH:27].[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[C:10]1=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10642402(S)-Benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-YL)acetate

Product 1

HCID 70271136(S)-Benzyl 2-(3-amino-2-oxopiperidin-1-yl)acetate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of compound 40 (4.00 g, 0.0110 mole) in 10 mL of ethyl acetate at room temperature was added 5N HCl in 5 ethyl acetate (50 mL, freshly prepared, 0.25 mole) in one portion. The solution was stirred for 3 hrs, solvent was evaporated, CH2Cl2 was added and the solvents were reevaporated. The residue was pumped at <1 mm Hg on a vacuum pump for 24 hours to afford 3.37 g (~Quantitative crude yield) of product 41 as a colorless foam. TLC (silica gel; CH2Cl2, methanol, conc. NH4OH: 27:3:1): Rf=0.32.

Workup

  1. customfreshly prepared
  2. customsolvent was evaporated
  3. additionCH2Cl2 was added
  4. customthe solvents were reevaporated
  5. waitThe residue was pumped at <1 mm Hg on a vacuum pump for 24 hours
  6. customto afford

Sources & evidence

ORD record
ord-0a5a552f7d3b4bdc836b500067fb6498
Source dataset
uspto-grants-2000_03
Patent number
US06034215

Reaction notes

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