Acetic Anhydride → HCID 66787411, compound

HRID 1947503Notes

Reaction equation

HRID 1947503 reaction equation
Cl.[C:2]([O:6][C:7]([N:9]1[CH2:14][C@@H:13]2[CH2:15][CH2:16][C@H:10]1[CH2:11][NH:12]2)=[O:8])([CH3:5])([CH3:4])[CH3:3].[C:17](OC(=O)C)(=[O:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:2]([O:6][C:7]([N:9]1[CH2:14][C@@H:13]2[CH2:15][CH2:16][C@H:10]1[CH2:11][N:12]2[C:17](=[O:19])[CH3:18])=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 45789462HCID 45789462, compound

Product 1

HCID 66787411HCID 66787411, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S,S)-2,5-diaza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester hydrochloride (645 mg, 2.59 mmol) in DCM (26 mL) was added acetic anhydride (490 μL, 5.19 mmol) and triethylamine (1.08 mL, 7.77 mmol) and the mixture was stirred (rt, 16 h). The reaction mixture was washed with water (3×8 mL) and brine (1×8 mL). The organic layer was dried, filtered and concentrated in vacuo to provide (S,S)-5-acetyl-2,5-diaza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (658 mg, 100%). This intermediate was dissolved in DCM (3.5 mL), treated with HCl (4 M in dioxane, 3.5 mL) and stirred (rt, 16 h). The dispersion was concentrated in vacuo to provide the title compound as a beige powder (494 mg, 100%). MS (ESI): mass calcd. for C8H14N2O, 154.11; m/z found, 155.2 [M+H]+. 1H NMR (500 MHz, MeOD): 4.71 (s, 0.5H), 4.25 (s, 0.5H), 3.97 (dt, J=12.1, 2.8, 0.5H), 3.87 (d, J=2.6, 1H), 3.84-3.73 (m, 1H), 3.68 (m, 1H), 3.64 (dd, J=13.8, 1.6, 0.5H), 3.54 (m, 0.5H), 3.45 (m, 1.5H), 2.12 (m, 4.5H), 2.06-1.91 (m, 2.5H).

Workup

  1. washThe reaction mixture was washed with water (3×8 mL) and brine (1×8 mL)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dafe56633b9a400c86dd92078057c89f
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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