Water → HCID 22235399, compound

HRID 1743713Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (3.08 g, 14.5 mmol; from Preparation B above) in 2-propanol (200 mL) was added H2O (20 mL) and 4-(2-oxiranylmethoxy)benzonitrile (2.54 g, 14.5 mmol; prepared as described in international patent application WO 99/31100). The resulting solution was warmed to 75° C., stirred for 18 h, cooled and concentrated in vacuo. Flash chromatography of the residue on silica gel eluting with CH2Cl2:EtOAc (3:1 to 2:1 gradient) gave 3.86 g (69%) of the sub-title compound.

Workup

temperaturecooled
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6805ffd31d9f43e2bfef6b689dcb862e
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012074B2

Reaction notes

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