Acetic Acid → HCID 12146692, compound

HRID 2301177Notes

Reaction equation

HRID 2301177 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[C:18]1([CH2:21][CH2:22][NH:23][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1001PhenethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12146692HCID 12146692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-4-oxo-1-piperidinecarboxylate in methylene chloride was added 2-phenethylamine, NaBH(OAc)3 and HOAc. The mixture was stirred at ambient temperature for 16 hours and quenched by addition of H2O. The aqueous layer was neutralized with NaHCO3 and extracted with CH2Cl2. The combined organic layer was washed with saturated NaHCO3 and brine and dried over MgSO4. Evaporation of solvent gave an off-white solid. This material was used without further purification. ESI-MS 305 (M+H); HPLC A: 2.54 min.

Workup

  1. customquenched by addition of H2O
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave an off-white solid
  7. customThis material was used without further purification
  8. custom2.54 min.

Sources & evidence

ORD record
ord-97b0bb5621424614b734dfde30eeb66b
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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