(S)-4-(Oxiran-2-ylmethoxy)benzonitrile → tert-Butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 898759Notes

Reaction equation

HRID 898759 reaction equation
[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]2.[O:17]1[CH2:19][C@H: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.O>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([O:21][CH2:20][C@@H:18]([OH:17])[CH2:19][N:7]2[CH2:6][CH:5]3[O:9][CH:1]([CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]3)[CH2:8]2)=[CH:23][CH:24]=1)#[N:27]

Participants

4

Reactant 2

HCID 6934187(S)-4-(Oxiran-2-ylmethoxy)benzonitrileHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 21076121tert-Butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

A mixture of tert-butyl 9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (prepared in an analogous fashion to the compound of Preparation A(vi) above; 0.72 g, 3.2 mmol) and 4-[(2S)-oxiranylmethoxy]benzonitrile (from step (i) above; 0.56 g, 3.2 mmol) in IPA/water (11 mL of 10:1) was stirred at 60° C. for 18 h. The solvent was then evaporated to give 1.3 g (100%) of the sub-title compound, which was used in the next step without further purification.

Workup

  1. customprepared in an analogous fashion to the compound of Preparation A(vi) above
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-4ff4d5c0cffc4ec4a94fcd6346092852
Source dataset
uspto-grants-2008_04
Patent number
US07351821B2

Reaction notes

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