Methylamine → N-(tert-Butoxycarbonyl)-N'-methylethylenediamine

Temperature

42.5 °C

With reference to FIG. 10c, BocNHCH2CH2OMs (32) (1.42 g, 5.94 mmol) was transferred to a Chem-Glass pressure vessel using minimum amount of THF to which 60 mL of methylamine (MeNH2, P/N: Aldrich 395056, 2.0 M in THF, 120 mmol) solution was added, capped and heated (while stirring) at 40-45° C. for 3 h, then at RT for overnight (use safety shield). TLC analysis (1:1 EtOAc-hexanes) showed complete consumption of 32 and formation of a new product (Rf 33=0.38; 1:1 DCM-MeOH+1% (v/v) Et3N; TLC plate was heated first for 5 min to remove Et3N then developed by heating with 3% (w/v) ninhydrin solution in EtOH). Reaction mixture then concentrated to an oil and purified by column chromatography (40 g SiO2 column Isco.; 40 mL/min, Column equilibrated with EtOAc, eluted with 1:1 MeOH-DCM+1% Et3N (v/v). 18 mL-fractions collected; fractions 13-19 had pure product) to give BocNH13CH213CH2NHMe 33 as colorless oil (0.79 g, 76%).). ES-MS (Direct infusion in MeOH) Calculated MH+ [13C2C6H18N2O2+H]+=177.14, observed MH+=177.14.

1. additionwas added
2. customcapped
3. temperatureheated
4. waitat RT for overnight (use safety shield)
5. customconsumption of 32 and formation of a new product (Rf 33=0.38
6. temperatureTLC plate was heated first for 5 min
7. customto remove Et3N
8. temperatureby heating with 3% (w/v) ninhydrin solution in EtOH)
9. customReaction mixture
10. concentrationthen concentrated to an oil
11. custompurified by column chromatography (40 g SiO2 column Isco.; 40 mL/min, Column equilibrated with EtOAc, eluted with 1:1 MeOH-DCM+1% Et3N (v/v). 18 mL-fractions collected; fractions 13-19 had pure product)

ORD record

ord-d627224a9db24ef88ed2cc18ff458986

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853133B2