Exo-2-bornanamine → HCID 10016039, compound

HRID 475351Notes

Reaction equation

HRID 475351 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[CH2:14]1[CH:18]2[CH2:19][CH:20]([NH2:21])[CH:16]([CH2:17]2)[CH2:15]1>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C@H:16]12[CH2:17][C@H:18]([CH2:14][CH2:15]1)[CH2:19][C@H:20]2[NH:21][CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4]

Participants

5

Reactant 2

HCID 98480Exo-2-bornanamineHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10016039HCID 10016039, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.03 g, 0.152 mmol) in acetonitrile (1 mL) at room temperature was added exo-2-aminonorborane (0.036 mL, 0.305 mmol) and a catalytic amount of tetrabutylammonium iodide. The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol:dichloromethane to provide the titled compound. MS (CI) m/z 271 (M+1)+; 1H NMR (300 MHz, MeOH-d4): δ ppm 4.7-4.8 (m, 2H), 3.61-3.8 (m, 2H), 3.2-3.3 (m, 1H), 3.02-3.11 (1H, s), 2.62-2.72 (m, 1H), 2.37-2.44 (m, 3H), 2.2-2.3 (br s, 2H), 1.0-1.7 (m, 8H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol

Sources & evidence

ORD record
ord-d1641055726e48eb987f6aad0decc906
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

Loading…