Tetrahydrofuran → 3-[(1r)-1-(4-Methylphenyl)ethyl]amino-1-propanesulfonic acid

HRID 239742Notes

Reaction equation

CO[C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH2:11])[CH3:10])=[CH:5][CH:4]=1.[CH2:12]1[CH2:18][S:15](=[O:17])(=[O:16])[O:14][CH2:13]1.O1CCC[CH2:20]1>>[CH3:20][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:11][CH2:13][CH2:12][CH2:18][S:15]([OH:14])(=[O:17])=[O:16])[CH3:10])=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 14264Propane sultone

HCID 641449(R)-1-(4-Methoxyphenyl)ethylamine

Product 1

HCID 119766413-[(1r)-1-(4-Methylphenyl)ethyl]amino-1-propanesulfonic acid

Procedure

To a solution of (R)-(+)-1-(4-methoxyphenyl)ethylamine (5.83 g, 38.6 mmol) in tetrahydrofuran (25 mL) was slowly added 1,3-propanesultone (4.56 g, 36.8 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with THF (25 mL) and acetone (25 mL). The solid was suspended in EtOH (200 mL). The suspension was stirred at reflux for 15 min. The solid was collected by filtration, washed with cold EtOH (50 mL), and dried in a vacuum oven (50° C.), to afford compound FN (5.6 g, 56%). 1H NMR (D2O, 500 MHz) δ ppm 7.26 (d, 2H, J=8.3 Hz), 6.90 (d, 2H, J=8.3 Hz), 4.22 (m, 1H), 3.68 (s, 3H), 2.92 (m, 1H), 2.76 (m, 3H), 1.90 (m, 2H), 1.49 (d, 3H, J=6.8 Hz). 13C NMR (D2O, 125 MHz) 8 ppm 159.87, 129.34, 128.18, 114.85, 57.99, 55.58, 48.05, 44.21, 21.45, 18.21. ES-MS 272 (M−1).

Workup

temperatureat reflux for 4 hours
filtrationThe solid was collected by filtration
washwashed with THF (25 mL) and acetone (25 mL)
stirringThe suspension was stirred
temperatureat reflux for 15 min
filtrationThe solid was collected by filtration
washwashed with cold EtOH (50 mL)
customdried in a vacuum oven (50° C.)
customto afford compound FN (5.6 g, 56%)

Sources & evidence

ORD record: ord-c62493d936ac47b29f58267c4e6fa8c5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642801B2

Reaction notes

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