4-(2-Oxiranylmethoxy)benzenecarbonitrile → HCID 53839837, compound

HRID 1596438Notes

Reaction equation

[CH:1]12[CH2:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[O:11])[CH2:2]2.[O:18]1[CH2:20][CH:19]1[CH2:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>CC(O)C.O>[C:27]([C:26]1[CH:29]=[CH:30][C:23]([O:22][CH2:21][CH:19]([OH:18])[CH2:20][N:7]2[CH2:8][CH:1]3[CH2:9][CH:5]([CH2:4][N:3]([C:10]([O:12][C:13]([CH2:16][CH3:17])([CH3:14])[CH3:15])=[O:11])[CH2:2]3)[CH2:6]2)=[CH:24][CH:25]=1)#[N:28]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Pentyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.0 g; 4.16 mmol; from step (b) above) was dissolved in IPA:H2O (9:1; 4 mL) and 4-(2-oxiranylmethoxy)benzonitrile (1.46 g; 8.32 mmol; see Example A above) was added to the resultant solution. The reaction mixture was stirred at 60° C. for 3 h, concentrated and the residue subjected to column chromatography (DCM:MeOH; gradient 1:0 to 68:32) giving the title compound (1.45 g).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-f19a99ad30a5485db243f2ccb379249d
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291475B1

Reaction notes

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