Triethylamine → HCID 89662240, compound

HRID 2275991Notes

Reaction equation

HRID 2275991 reaction equation
[CH2:1]([C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:11])([CH3:10])[C:5]=1[CH2:12][C:13]([OH:15])=O)[CH:2]=[CH2:3].C(N=C=N[CH2:21][CH2:22][CH2:23][N:24]([CH3:26])C)C.ON1C2N=CC=CC=2N=N1.N1CCCC1.CCN(CC)CC>CN(C=O)C.O>[CH2:1]([C:4]1[CH2:9][CH2:8][CH2:7][C:6]([CH3:10])([CH3:11])[C:5]=1[CH2:12][C:13]([N:24]1[CH2:23][CH2:22][CH2:21][CH2:26]1)=[O:15])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 181649HOAtHCID 89650178HCID 89650178, compound

Product 1

HCID 89662240HCID 89662240, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-allyl-6,6-dimethyl-cyclohexen-1-yl)acetic acid (80 mg, 0.38 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (103 mg, 0.54 mmol) and 1-hydroxy-7-azabenzotriazole (73 mg, 0.54 mmol) in DMF (2 mL) was added the pyrrolidine (55 mg, 0.77 mmol) followed by Et3N (117 mg, 1.15 mmol). The solution was stirred under Ar for 18 h. Water was added (20 mL) and the solution was extracted with ether (3*20 mL). The combined organic layers were washed with water (3*30 mL) and brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (4-1 to 3/1) to give the title compound as colourless oil (82 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 5.75 (1H, ddt, J=16.7, 10.5, 6.1, 6.1 Hz), 4.93 (2H, m, J=19.1, 1.8 Hz), 4.93 (0H, dd, J=8.1, 1.8 Hz), 3.44 (4H, td, J=6.8, 4.0 Hz), 2.93 (2H, s), 2.64 (2H, d, J=5.9 Hz), 1.89-2.02 (4H, m), 1.82 (2H, quin, J=6.6 Hz), 1.58 (2H, d, J=11.7 Hz), 1.43-1.50 (2H, m) 0.90-0.99 (6H, s) ppm.

Workup

  1. extractionthe solution was extracted with ether (3*20 mL)
  2. washThe combined organic layers were washed with water (3*30 mL) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with cyclohexane and ethyl acetate (4-1 to 3/1)

Sources & evidence

ORD record
ord-47b1358c5c934385bc00ebf54ce13a31
Source dataset
uspto-grants-2015_09
Patent number
US09131688B2

Reaction notes

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