HCID 57461146, compound → HCID 141306036, compound

HRID 2066882Notes

Reaction equation

HRID 2066882 reaction equation
C([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]1=O)(OC(C)(C)C)=O.[NH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>C(O)C>[CH:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][CH:17]([O:16]/[N:15]=[C:8]2\[CH2:9][NH:10][CH2:11][CH2:12][CH2:13]\2)[CH2:22][CH2:21]1)=[O:24])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 57461146HCID 57461146, compoundHCID 67512109HCID 67512109, compound

Product 1

HCID 141306036HCID 141306036, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

3-Boc-piperidinone (0.83 mmol) and NaOAc.3H2O (30 mg) were combined in 1 mL of ethanol and heated to 65° C. for 15 minutes. 2b (167 mg, 0.83 mmol) was added and the mixture was heated at 65° C. for 18 h. The mixture was concentrated, taken up with DCM (5 mL), washed with aqueous NaHCO3 (5 mL) and the organic layer was separated and treated with TFA (5 mL). The mixture was stirred at room temperature for 45 minutes, concentrated, diluted with NaHCO3 (8 mL) and extracted with EtOAc (2×5 mL). The extracts were dried and concentrated to afford the crude 61a: LC-MS 284.2 (MH+).

Workup

  1. temperaturethe mixture was heated at 65° C. for 18 h
  2. concentrationThe mixture was concentrated
  3. washwashed with aqueous NaHCO3 (5 mL)
  4. customthe organic layer was separated
  5. additiontreated with TFA (5 mL)
  6. concentrationconcentrated
  7. additiondiluted with NaHCO3 (8 mL)
  8. extractionextracted with EtOAc (2×5 mL)
  9. customThe extracts were dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c566d155810e489d948df75b7f0f2f59
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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