ChemicalBook CAS DataBase List (S,S)-3-CBZ-3,6-DIAZABICYCLO[3.2.0]HEPTANE

(S,S)-3-CBZ-3,6-DIAZABICYCLO[3.2.0]HEPTANE synthesis

10synthesis methods

Product Name:(S,S)-3-CBZ-3,6-DIAZABICYCLO[3.2.0]HEPTANE
CAS Number:370881-43-9
Molecular formula:C13H16N2O2
Molecular Weight:232.28

benzyl 3-(tert-butoxycarbonylamino)-4-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

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(S,S)-3-CBZ-3,6-DIAZABICYCLO[3.2.0]HEPTANE

370881-43-9
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$285.00/100mg

Yield:370881-43-9 97%

Reaction Conditions:

with trifluoroacetic acid in ethanol;dichloromethane;

Steps:

52.D benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

EXAMPLE 52D benzyl (1S,5S)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate The product of Example 52C (43.7 g, 125 mmol) in CH₂Cl₂ (150 mL) was treated with trifluoroacetic acid (50 mL) at room temperature and allowed to stir for 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in ethanol (250 mL) and basified to pH 10 with 10% aqueous NaOH. The mixture was warmed to 60° C. at 10 hours. The reaction was allowed to cool to room temperature and was concentrated under reduced pressure to remove most of the ethanol. The residue was extracted with CHCl₃ (2*500 mL). The extracts were combined, washed with brine (3*50 mL) and then passed through a short column of diatomaceous earth. The filtrate was concentrated to provide the title compound as a yellow oil (28.0 g, 97%) which was used in the next step without further purification. ¹H NMR (MeOH-d₄, 300 MHz) δ 3.30-3.16 (m, 3H), 3.36 (m, 1H), 3.82 (m, 3H), 4.55 (m, 1H), 5.20 (s, 2H), 7.36 (m, 5H); MS (DCI/NH₃) m/z 250 (M+NH₄)⁺, 233 (M+H)⁺.

References:

US2002/19388,2002,A1