Practical synthesis of (3S,4S)-3-methoxy-4-methylaminopyrrolidine

Synthesis of 3‐Hydroxy‐ and 3‐Carboxy‐Δ2‐isoxazoline Amino Acids and Evaluation of Their Interaction with GABA Receptors and Transporters

“…Similarly, amino acids 12 and 13 were prepared with the strategies described above with 1-(tert-butoxycarbonyl)-3-pyrroline [18] as the dipolarophile (Scheme 3). The final compound 12 was purified as its zwitterion by ion-exchange column chromatography with Amberlite IR-120 (H + form), and 10 % aqueous pyridine as the eluent.…”

“…All reagents were purchased from Aldrich. 1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine 18, [14] 1-(tert-butoxycarbonyl)-3-pyrroline 23, [18] (Ϯ)-cyclopent-2-en-1-ol (Ϯ)-28, [25] dibromoformaldoxime [16] and ethyl 2-chloro-2-(hydroxyimino)acetate [17] were prepared according to literature procedures. (7 g).…”

Synthesis of (±)‐trans‐hexahydropyrrolo[3,4‐d]oxazol‐2‐one and its derivatives by using N‐(tert‐butyloxycarbonyl)‐3‐pyrroline as precursor

“…Reaction of 1b with N-bromosuccinimide (NBS) in DMSO-H 2 O at room temperature afforded the racemic trans bromohydrin (7) [13]. The 1 H NMR spectra of the latter product revealed disappearance the triplet corresponding to alkenyl protons at d 5.78 ppm, whereas broad singlet for hydroxyl signal appeared at d 2.8 ppm and also the mass spectrum showed in addition to molecular ion peak, bromine isotopic peak (M þ þ2) at m/z 268.…”

The synthesis of phosphonic acids derived from homocysteine via transesterification reactions

“…The yield from the reaction was 10.5 g (74%). Alternatively, compound 6a was prepared according to procedure described by Van der Veken et al 15 Aldehyde 1a (2 g; 12 mmol), tert-butyl carbamate 20 (1.2 g; 10 mmol) and triphenyl phosphite (3.1 g; 10 mmol) were dissolved in 25 ml of dry dichloromethane. TiCl 4 (0.1 eq, 0.1 M solution) was added in one portion.…”