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

HRID 1584572Notes

Reaction equation

HRID 1584572 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.Cl.C(Cl)[Cl:29].[NH4+].[OH-]>C(OCC)(=O)C.CO>[ClH:29].[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 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 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the compound of Example 38 (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 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
  7. custom3.37 g (~Quantitative crude yield) of product as a colorless foam

Sources & evidence

ORD record
ord-b814c23aab444e8c9962a29cf0daa8ca
Source dataset
uspto-grants-1999_08
Patent number
US05932733

Reaction notes

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