Potassium Carbonate → 1-(3-(3-Aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol

HRID 658811Notes

Reaction equation

[CH2:1]([C:3]([OH:24])([CH2:22][CH3:23])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH:15]C(=O)C(F)(F)F)[CH:9]=[CH:10][CH:11]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[NH2:15][CH2:14][CH2:13][CH2:12][C:8]1[CH:7]=[C:6]([C:5]#[C:4][C:3]([CH2:22][CH3:23])([OH:24])[CH2:1][CH3:2])[CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 45 °C

Procedure

N-(3-(3-(3-ethyl-3-hydroxypentyl)phenyl)propyl)-2,2,2-trifluoroacetamide (12) (0.660 g, 1.93 mmol) was dissolved in MeOH (15 mL), and an aqueous solution of K2CO3 (0.42 g/3 mL) was added. The resulting mixture was stirred at 45° C. for 4 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure then partitioned between EtOAc (50 mL) and water (50 mL). The combined organics were dried over Na2SO4, and concentrated under reduced pressure. Purification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient) gave 1-(3-(3-aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol (13) as a light yellow oil. Yield (0.421 g, 89%): 1H NMR (400 MHz, DMSO-d6) δ 7.15-7.26 (m, 4H), 5.11 (s, 1H), 2.56 (t, J=7.6 Hz, 2H), 2.47 (t, J=5.2 Hz, 2H), 1.55-1.65 (m, 6H), 1.39 (br s, 2H), 0.97 (t, J=7.6 Hz, 6H).

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
customthen partitioned between EtOAc (50 mL) and water (50 mL)
dry with materialThe combined organics were dried over Na2SO4
concentrationconcentrated under reduced pressure
customPurification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient)

Sources & evidence

ORD record: ord-0c33eeea74b345cb872f1cf8bc252048
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076516B2

Reaction notes

Loading…