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

HRID 2180011Notes

Reaction equation

HRID 2180011 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[OH:14][C:15]1([CH3:31])[CH:20]2[CH2:21][NH:22][CH2:23][CH:16]1[CH2:17][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2>C(#N)C.O>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:22]2[CH2:21][CH:20]3[C:15]([OH:14])([CH3:31])[CH:16]([CH2:17][N:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)[CH2:23]2)=[CH:7][CH:8]=1)#[N:11]

Participants

4

Reactant 2

HCID 6934187(S)-4-(Oxiran-2-ylmethoxy)benzonitrileHCID 22490276Tert-butyl 9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 57173795tert-butyl 7-[(2S)-3-(4-cyanophenoxy)-2-hydroxypropyl]-9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

4-[(2S)-Oxiranylmethoxy]benzonitrile (from step (v) above, 247 mg, 1.4 mmol) was added to a stirred solution of tert-butyl 9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (iv) above, 328 mg, 1.28 mmol) in acetonitrile:water (4:1). The reaction was heated to 60° C. for 12 h, after which stirring was continued at rt for a further 48 h.

Sources & evidence

ORD record
ord-d3a2469425ff4bb3b08bb0bbcb243714
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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