Benzylamine → HCID 18767798, compound

HRID 479951Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:19][CH2:18][CH:17](OS(C)(=O)=O)[CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH2:25]([NH:32][CH:17]1[CH2:18][CH2:19][N:15]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[CH2:16]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of methanesulfonic acid 1-(4-butoxy-benzenesulfonyl)-pyrrolidin-3-yl ester (1.51 g, 4 mmol) in tetrahydrofuran (8 ml) was added benzylamine (3.46 g, 32 mmol) and the mixture was stirred at 100° C. for 2 days. After cooling to room temperature the tetrahydrofuran was evaporated, and the residue washed with hexanes. The solid was stirred with 10% sodium carbonate solution (30 ml) and ethyl acetate (40 ml), and the organic solution was washed brine, dried over anhydrous sodium sulfate, and filtered through Magnolsol. The filtrate was evaporated, and the residue was washed with hexanes to give 1.49 g of a white solid; m.p. 99-100° C.; MS (ES) m/z 389.0 (MH+); HRMS (EI) Calcd. for C21H28N2O3S (M+): 388.1820, Found: 388.1826.

Workup

customwas evaporated
washthe residue washed with hexanes
stirringThe solid was stirred with 10% sodium carbonate solution (30 ml) and ethyl acetate (40 ml)
washthe organic solution was washed brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered through Magnolsol
customThe filtrate was evaporated
washthe residue was washed with hexanes

Sources & evidence

ORD record: ord-d4c9c4c0d5d0432d8f9e346d78cb39cb
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649603B2

Reaction notes

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