Benzyl 7-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate → tert-butyl (1S)-2-(4-cyanophenoxy)-1-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-ylmethyl)ethylcarbamate

HRID 500483Notes

Reaction equation

HRID 500483 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=1)[CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][N:15](C(OCC3C=CC=CC=3)=O)[CH2:16]2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:38]([C:35]1[CH:34]=[CH:33][C:32]([O:31][CH2:30][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:10][N:11]2[CH2:18][CH:17]3[O:19][CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)=[CH:37][CH:36]=1)#[N:39]

Participants

5

Reactant 2

HCID 68459937Benzyl 7-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86588969tert-butyl (1S)-2-(4-cyanophenoxy)-1-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-ylmethyl)ethylcarbamateYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 7-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)propyl]-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (from step (ix) above; 2.55 g, 4.7 mmol) in 95% ethanol (50 mL) was hydrogenated over 5% Pd/C (0.8 g) at 30 kPa. When the quantity of hydrogen calculated for complete reaction had been consumed, the reaction was stopped. The mixture was filtered through Celite®, and the filtrate concentrated in vacuo. The resulting residue was purified by chromatography on silica, eluting with CHCl3:ammoniacal methanol (95:5), to yield the title compound 1.39 g (75%).

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting residue was purified by chromatography on silica
  5. washeluting with CHCl3

Sources & evidence

ORD record
ord-474461ef6e414dcab72da7bcd466c917
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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