Triethylamine → HCID 60203567, compound

HRID 1844077Notes

Reaction equation

HRID 1844077 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=O)[CH:2]=[CH2:3].Cl.[CH3:15]N(C)CCCN=C=NCC.ON1[C:31]2[N:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([N:32]1[C@H:33]([CH3:15])[CH2:34][CH2:35][C@H:30]1[CH3:31])=[O:13])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22590982HCID 22590982, compound

Product 1

HCID 60203567HCID 60203567, compoundYield 378.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-allyl phenyl acetic acid (0.050 mg, 0.284 mmol) in Dimethylformamide (5 mL) was added 3-[3-(Dimethylamino)propyl]-1-ethylcarbodiimide hydrochloride (EDCI, 0.075 mmol, 0.397 mmol), 1-Hydroxy-7-azabenzotriazole (HOAt, 0.054 mg, 0.397 mmol), (2R,5R)-dimethylpyrrolidine (0.034 mL, 0.298 mmol) followed by triethylamine (0.118 mL, 0.851 mmol). The solution was stirred for 18 h and water was added (20 mL). The aqueous layer was extracted with diethylether and the combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (9/1 the 4/1) to give 2-(2-allyl-phenyl)-1-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-ethanone (colourless oil, 73 mg, 99%). C17H23NO; MW: 257.38; LCMS (method A) RT 1.84 min; ES 258 (100%, MH+), 280 (10%, MNa+); 1H NMR (400 MHz, CDCl3) δ 7.08-7.24 (4H, m), 5.97 (1H, m), 5.07 (1H, m), 4.99 (1H, m), 4.29 (1H, q), 4.01 (1H, q), 3.76 (1H, d), 3.58 (1H, d), 3.39 (2H, m), 2.08-2.26 (2H, m), 1.52-1.63 (2H, m), 1.23 (3H, d), 1.21 (3H, d) ppm.

Workup

  1. extractionThe aqueous layer was extracted with diethylether
  2. washthe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with cyclohexane and ethyl acetate (9/1 the 4/1)

Sources & evidence

ORD record
ord-8a341f9bb68e4d769e68c4f901bc7061
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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