Hydrochloric Acid → tert-Butyl (1S)-2-(4-cyanophenoxy)-1-{[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]methyl}ethylcarbamate

HRID 411550Notes

Reaction equation

HRID 411550 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][N:12]([CH2:17][C@H:18]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1)[CH2:13]2)C1C=CC=CC=1.Cl>[Pd].CO>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C@@H:18]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:17][N:12]2[CH2:13][CH:14]3[CH:9]([NH:8][CH3:1])[CH:10]([CH2:16][CH2:15]3)[CH2:11]2)=[CH:26][CH:25]=1)#[N:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90929600tert-butyl (1S)-2-{8-[benzyl(methyl)amino]-3-azabicyclo-[3.2.1]oct-3-yl}-1-[(4-cyanophenoxy)methyl]ethylcarbamate

Product 1

HCID 91385514tert-Butyl (1S)-2-(4-cyanophenoxy)-1-{[8-(methylamino)-3-azabicyclo-[3.2.1]oct-3-yl]methyl}ethylcarbamateYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl (1S)-2-{8-[benzyl(methyl)amino]-3-azabicyclo[3.2.1]oct-3-yl}-1-[(4-cyanophenoxy)methyl]ethylcarbamate (0.8 g, 1.6 mmol), 1 M HCl (0.8 mL) and MeOH (30 mL) was hydrogenated over 5% Pd/C. The reaction was stopped when the amount of H2 calculated for complete reaction had been consumed. The mixture was filtered through silica and the filtrate evaporated. The resulting crude product was purified on silica gel, eluting with DCM:ammoniacal methanol (9:1), to yield 0.4 g (61%) of the title compound.

Workup

  1. customcalculated for complete reaction
  2. customhad been consumed
  3. filtrationThe mixture was filtered through silica
  4. customthe filtrate evaporated
  5. customThe resulting crude product was purified on silica gel
  6. washeluting with DCM

Sources & evidence

ORD record
ord-266e4cf9c3784dee8361dc246da7191e
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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