3-Benzyl-3,8-diazabicyclo[3.2.1]octane → tert-Butyl (1S)-2-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-1-[(4-cyanophenoxy)methyl]ethylcarbamate

HRID 1743733Notes

Reaction equation

HRID 1743733 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][C@@H:9]2[CH2:11][N:10]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2].[CH2:21]([N:28]1[CH2:34][CH:33]2[NH:35][CH:30]([CH2:31][CH2:32]2)[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[CH2:21]([N:28]1[CH2:34][CH:33]2[N:35]([CH2:11][C@H:9]([NH:10][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:8][O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:20][CH:19]=3)[CH:30]([CH2:31][CH2:32]2)[CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octaneHCID 86588968tert-Butyl (2S)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate

Product 1

HCID 86759944tert-Butyl (1S)-2-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-1-[(4-cyanophenoxy)methyl]ethylcarbamateYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl (2S)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate (3 g, 11 mmol; see step (d) above) and 3-benzyl-3,8-diazabicyclo[3.2.1]octane (2.2 g, 0.011 mol; from Preparation B, step (e) above) were mixed in isopropanol (50 mL) and stirred at 60° C. for 48 h, and then at 80° C. for 2 h. The solvent was evaporated and the residue purified by chromatography, eluting with DCM/MeOH (9:1), to give the sub-title compound in 77% yield.

Workup

  1. waitat 80° C. for 2 h
  2. customThe solvent was evaporated
  3. customthe residue purified by chromatography
  4. washeluting with DCM/MeOH (9:1)

Sources & evidence

ORD record
ord-07a8698a095b46cf847e8ed8cea381dd
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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