Water → HCID 68557503, compound

HRID 2036086Notes

Reaction equation

HRID 2036086 reaction equation
N12CCCN=C1CCCC[CH2:2]2.[NH:12]([CH2:19][C:20]1([OH:36])[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:21]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH2:37]>C(#N)C>[O:37]=[C:2]1[N:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:19][C:20]2([CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[CH2:21]2)[O:36]1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68558470Phenylmethyl 3-hydroxy-3-[(phenylamino)methyl]-1-piperidinecarboxylate

Product 1

HCID 68557503HCID 68557503, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

N,N′-Carbonyldiimidazole (1.5 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 g) were added to benzyl 3-(anilinomethyl)-3-hydroxypiperidine-1-carboxylate (2.2 g) obtained by the above-mentioned reaction in acetonitrile (35 mL), and the mixture was stirred at 80° C. for 20 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (25% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give crude benzyl 2-oxo-3-phenyl-1-oxa-3,7-diazaspiro[4.5]decane-7-carboxylate (2.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b6a6d5cb064e4c41abbf11c5d2488765
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

Loading…