Reaction #66055

Reaction equation

186

Di-tert-butyl N-3-butenyliminodicarboxylate

trifluoroacetic acid

→

title compound

Yield 96.0%

tert-Butyl N-3-butenylcarbamate

Yield 96.0%

Solvents

DCM

Conditions

Workup

1. 1
   Otherbefore being quenched with 2M NaOH (25 mL)
2. 2
   Extractionextracted with DCM (3×20 mL)
3. 3
   OtherThe combined organic fractions were dried
4. 4
   Concentrationconcentrated

Procedure

To a solution of 186 (708 mg, 2.61 mmol) in DCM (20 mL) was added trifluoroacetic acid (593 mg, 5.20 mmol) and the mixture was allowed to stir for 5 min before being quenched with 2M NaOH (25 mL) and extracted with DCM (3×20 mL). The combined organic fractions were dried, and concentrated to yield the title compound (429 mg, 2.50 mmol, 96%) as a light brown oil, which had spectral data in agreement with that reported.104 1H NMR (CDCl3, 300 MHz): δ 5.75 (m, 1H, H3); 5.08 (m, 2H, H4); 4.59 (bs, 1H, NH); 3.20 (dd, J=6.3, 12.6 Hz, 2H, H1); 2.24 (dd, J=6.9, 12.6 Hz, 2H, H2); 1.44 (s, 9H, (CH3)3). Mass Spectrum (ES, +ve) m/z 116 (100%) [MH+] less 56 (Boc rearrangement].

Source