tert-Butyl 8-benzyl-3,8-diazabicyclo[3.2.1]octane-3-carboxylate → Ammonium Hydroxide

HRID 1246708Notes

Reaction equation

HRID 1246708 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[NH4+:8].[OH-:17].[CH:9]12[NH:8][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10]2

Participants

5

Reactant 1

HCID 21904744tert-Butyl 8-benzyl-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 21904757tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 8-benzyl-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (5.46 mmol, 203 mg) and Pearlman's catalyst were combined in methanol under a hydrogen atmosphere (1 atmosphere) stirred overnight at room temperature. Purged with nitrogen, filtered off the catalyst, and concentrated the filtrate to a yellow liquid. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (5% MeOH, 0.5% NH4OH in CH2Cl2, then 10% MeOH, 1% NH4OH in CH2Cl2) to provide the title compound. MS (DCI/NH3) m/z: 213 (M+H)+; 1H NMR (CDCl3) δ 1.45 (s, 9H), 1.75 (br, 4H), 2.93 (d, 1H), 3.01 (d, 1H), 3.47 (d, 2H), 3.68 (d, 1H), 3.81 (d, 1H).

Workup

  1. customPurged with nitrogen
  2. filtrationfiltered off the catalyst
  3. concentrationconcentrated the filtrate to a yellow liquid
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (5% MeOH, 0.5% NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-6bbba370569346f08ae86deb5e522efd
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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