Trifluoroacetic acid → Tert-butyl but-3-EN-1-ylcarbamate

HRID 1664116Notes

Reaction equation

HRID 1664116 reaction equation
[CH2:1]([N:5](C(OC(C)(C)C)=O)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][CH:3]=[CH2:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12186469Di-tert-butyl N-3-butenyliminodicarboxylate

Product 1

HCID 11263760Tert-butyl but-3-EN-1-ylcarbamateYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 186 (708 mg, 2.60 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].

Workup

  1. custombefore being quenched with 2M NaOH (25 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. customThe combined organic fractions were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d001b085c4645b983ea29c8d3fe6312
Source dataset
uspto-grants-2011_10
Patent number
US08039430B2

Reaction notes

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