Ammonium Hydroxide → Ammonium Hydroxide

HRID 1246704Notes

Reaction equation

HRID 1246704 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-d992aaa1783b43178ac4cb359270d984
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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