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

HRID 1941448Notes

Reaction equation

HRID 1941448 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 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-58e0f9be418a4d4db11b2669de90b61f
Source dataset
uspto-grants-1997_12
Patent number
US05703208

Reaction notes

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