Benzyl(4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)carbamate → N1,N1-bis(2-methoxyethyl)-3-methylbutane-1,3-diamine

HRID 1056357Notes

Reaction equation

C(OC(=O)[NH:10][C:11]([CH3:24])([CH2:13][CH2:14][N:15]([CH2:20][CH2:21][O:22][CH3:23])[CH2:16][CH2:17][O:18][CH3:19])[CH3:12])C1C=CC=CC=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:23][O:22][CH2:21][CH2:20][N:15]([CH2:16][CH2:17][O:18][CH3:19])[CH2:14][CH2:13][C:11]([CH3:24])([NH2:10])[CH3:12]

Participants

Conditions

Temperature: 85 °C

Procedure

A glass microwave reaction vessel was charged with benzyl(4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)carbamate (500 mg, 1.42 mmol) in TFA/DCM (1:1, 4 mL). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc.) at 85° C. for 7 h. The solvent was removed and the residue was filtered through a plug of Si-carbonate (0.59 mmol/g) and washed with DCM (300 mL, 5% MeOH in DCM (200 mL) and the filtrate was concentrated to give N1,N1-bis(2-methoxyethyl)-3-methylbutane-1,3-diamine (310 mg, 1.42 mmol, 100% yield) as an orange oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.47 (4H, t, J=6.1 Hz), 3.34 (6H, s), 2.71 (4H, t, J=6.1 Hz), 2.60-2.67 (2H, m), 1.50-1.59 (2H, m), 1.10 (6H, s).

Workup

customA glass microwave reaction vessel
customThe solvent was removed
filtrationthe residue was filtered through a plug of Si-carbonate (0.59 mmol/g)
washwashed with DCM (300 mL, 5% MeOH in DCM (200 mL)
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-b25d7f8129e8477fb8f50a6443962568
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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