1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86679962, compound

HRID 1915750Notes

Reaction equation

HRID 1915750 reaction equation
[O:1]=[C:2]1[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][CH:7]=[CH:8]1.[CH:16](=[N:23]/[OH:24])\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1CCN2C(=NCCC2)CC1>CC#N>[CH:16](=[N:23][O:24][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:2](=[O:1])[CH2:8]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5324611Benzaldehyde OximeHCID 75464896tert-Butyl 3-oxo-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Product 1

HCID 86679962HCID 86679962, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(Z)-tert-butyl 3-oxo-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate (330 mg, 1.56 mmol), (E)-benzaldehyde oxime (286 mg, 2.36 mmol) and DBU (0.007 mL, 0.05 mmol) were combined in MeCN (0.5 mL) and the mixture was stirred at room temperature for 48 hr. The solvent was removed under reduced pressure and the residue purified via preparative HPLC to give tert-butyl 5-(benzylideneaminooxy)-3-oxoazepane-1-carboxylate as a brown oil (127 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified via preparative HPLC

Sources & evidence

ORD record
ord-c3049f0a0eaa4417ad3cf315df70d895
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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