Ammonium Hydroxide → Ammonium Hydroxide

HRID 1394076Notes

Reaction equation

HRID 1394076 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1)=[O:4].[OH-].[NH4+]>CO>[NH4+:5].[OH-:4].[CH:7]12[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:10]([CH2:9][CH2:8]1)[CH2:11][NH:5][CH2:6]2

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 21904733tert-Butyl 3-(trifluoroacetyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 3-(trifluoroacetyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (6.54 mmol) in methanol (85 mL) was treated with ammonium hydroxide (8.5 mL) and stirred overnight at room temperature. The mixture was concentrated under reduced pressure and 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 1.47 (s, 9H), 1.81 (m, 2H), 1.94 (m, 2H), 2.65 (dd, 2H), 3.00 (br, 2H), 4.11 (br, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by chromatography on silica gel (5% MeOH, 0.5% NH4OH in CH2Cl2

Sources & evidence

ORD record
ord-663ab3bfe5b945609efb4e976e1ea8a7
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

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