Diisopropylethylamine → HCID 22056694, compound

HRID 1923396Notes

Reaction equation

HRID 1923396 reaction equation
NC[CH:3]1[CH2:11][CH2:10][CH:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4]1([CH3:13])[CH3:12].[CH:14]([N:17](CC)C(C)C)(C)C>C(O)C>[C:14]([CH:11]1[CH2:10][CH:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4]([CH3:12])([CH3:13])[CH2:3]1)#[N:17]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 22056632HCID 22056632, compound

Product 1

HCID 22056694HCID 22056694, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±) Equatorial aminomethyl-2,2-dimethylazabicyclo[4.3.0]nonane (0.1 g, 0.0006 mole) was treated with mutilin 14-toluenesulfonyloxyacetate (0.25 g, 0.0005 mole), (K Biedl, J Antibiotics 29 (2), 133, 1976) and N,N-diisopropylethylamine (0.1 ml, 0.0006 mole) in ethanol (20 ml) and heated under reflux for 6 hours. The mixture was then concentrated in vacuo and the residue partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organics were separated and dried (Na2SO4). Chromatography on silica gel eluting with chloroform/methanol/35% ammonia solution (90:9:1) gave the title compound 0.08 g, (31%); 1H NMR (CDCl3) 0.71 (3H, d, J 6.5 Hz) 0.90 (3H, d, J 6.5 Hz), 0.95 (3H, s), 1.25-2.55 (38H, m), 2.85-2.97 (1H, m), 3.19-3.39 (2H, m), 5.15 (1H, d, J 16.5 Hz), 5.31 (1H, d, J 11.1 Hz), 5.78 (1H, d, J 8.6 Hz), 6.50 (1H, dd, J 15.0 and 11.1 Hz). MS (+ve ion electrospray) m/z 543 (MH+, 100%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue partitioned between saturated sodium hydrogen carbonate solution and dichloromethane
  5. customThe organics were separated
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-717be6f44bca45518933b173c12e530d
Source dataset
uspto-grants-2012_05
Patent number
USRE043390E1

Reaction notes

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