Undecylenic Acid → HCID 23137627, compound

HRID 707631Notes

Reaction equation

HRID 707631 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[C:12](O)(=[O:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:6]12[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7]1)[CH:4]([NH:3][C:12](=[O:23])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:5]2

Participants

5

Reactant 3

HCID 5634Undecylenic AcidHCID 81531DiisopropylethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 23137627HCID 23137627, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

An oven-dried 50 mL round bottom flask was charged with 3-aminoquinuclidine dihydrochloride (2 mmol), 10-undecenoic acid (2 mmol), N,N-dimethylaminopyridine (0.3 mmol), diisopropylethylamine (4 mmol), and dry DMF (15 mL). The flask was purged with argon and cooled to 0° C. in an ice bath. Dicyclohexycarbodiimide (2.2 mmol) was then add to the solution, the flask repurged with argon, and the mixture warmed to R.T. and stirred for 46 h. The reaction mixture was concentrated in vacuo and 30 ml diethyl ether added to the residue. The solid was filtered off over Celite and the organic phase concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate/hexanes (3:7) to afford the product as a white solid (23%). Rf=0.44. 1HNMR (400 MHz, CDCl3): δ=5.73 (m, 1H), 4.93 (dd, 1H, 3JHH=17.0 Hz, 4JHH=1.5 Hz), 4.87 (d, 1H, 3JHH=10.3 Hz), 3.71 (m, 1H), 2.10 (t, 2H, 3JHH=7.8 Hz), 1.97 (q, 2H, 3JHH=7.3 Hz), 1.85 (m, 2H), 1.54-1.68 (m, 5H), 1.02-1.34 (m, 15H) ppm. 13CNMR (400 MHz, CDCl3): δ=172.2, 139.1, 114.1, 48.6, 48.0, 37.0, 34.0, 33.7, 33.2, 29.3, 29.2, 29.0, 28.8, 25.9, 25.7, 25.5, 25.0, 24.9 ppm. HRMS-ESI: Calculated [M-C2H2]+: 266.2358. found: 266.2474.

Workup

  1. customThe flask was purged with argon
  2. additionDicyclohexycarbodiimide (2.2 mmol) was then add to the solution
  3. temperaturethe mixture warmed to R.T.
  4. concentrationThe reaction mixture was concentrated in vacuo and 30 ml diethyl ether
  5. additionadded to the residue
  6. filtrationThe solid was filtered off over Celite
  7. concentrationthe organic phase concentrated in vacuo
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-45dd71c375a94c9d88900a45400d5415
Source dataset
uspto-grants-2015_11
Patent number
US09175026B2

Reaction notes

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