Carbamate → (1S,2S)-1-Amino-2-ethylcyclopropanecarboxylic acid

To carbamate 14c (267 mg, 0.810 mmol) was added a 1.0 M TBAF solution in THF (1.62 mL, 1.62 mmol, 2.0 eq.). The reaction mixture was stirred overnight at RT, refluxed for 30 min and then diluted with AcOEt. The solution was successively washed with water (2×) and brine. After the usual treatment (MgSO4, filtration and concentration) the desired amine 14d was isolated (122 mg, 0.721 mmol, 89% yield) as a pale yellow liquid. 1H NMR (CDCl3) δ5.94-5.86 (m,1H), 5.31-5.22 (m, 2H), 4.58 (d, J=5.7 Hz, 2H), 1.75 (bs, 2H), 1.61-1.53 (m, 2H), 1.51-1.42 (m, 2H), 1.00 (t, J=7.3 Hz, 3H), 0.70-0.62 (m, 1H).

1. temperaturerefluxed for 30 min
2. washThe solution was successively washed with water (2×) and brine
3. filtrationAfter the usual treatment (MgSO4, filtration and concentration) the desired amine 14d
4. customwas isolated (122 mg, 0.721 mmol, 89% yield) as a pale yellow liquid

ORD record

ord-002b3e70b5d0421f8b9e9a23201325c2

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329379B1