Ethanol → HCID 88543298, compound

HRID 2168206Notes

Reaction equation

HRID 2168206 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[C:9](=O)[CH2:8][CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1.Cl.[NH2:19]O.[CH2:21]([OH:23])C>>[CH3:21][O:23]/[N:19]=[C:9]1\[CH:4]([CH2:3][O:2][CH3:1])[CH2:5][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:8]\1

Participants

4

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 67988189HCID 67988189, compound

Product 1

HCID 88543298HCID 88543298, compound

Conditions

Temperature
78 °C

Procedure

1,1-dimethylethyl 3-[(methyloxy)methyl]-4-oxo-1-piperidinecarboxylate D31 (1.2 g) and hydroxylamine hydrochloride (410 mg, 4.9 mmol) were dissolved in ethanol (60 ml). The reaction mixture was heated to 78° C. for 4 hours. Solvent was removed and dichloromethane (excess) was added. The organic layer was washed with water (3×), brine, collected and solvent removed to afford a yellow oil of the desired product D32 in 1.3 g. LCMS [M-56+H] 217.1@ 1.68 min (5 min run)

Workup

  1. customSolvent was removed
  2. additiondichloromethane (excess) was added
  3. washThe organic layer was washed with water (3×), brine
  4. customcollected
  5. customsolvent removed

Sources & evidence

ORD record
ord-b28329eab0c1475f8b94060a6a7f4e83
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

Loading…