(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 1374080Notes

Reaction equation

HRID 1374080 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-5f7b82504ead4232af7b8d0ebecdfb9f
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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