ChemicalBook CAS DataBase List 3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)-

3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)- synthesis

6synthesis methods

Product Name:3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)-
CAS Number:799279-81-5
Molecular formula:C10H18N2O2
Molecular Weight:198.26

3-benzyl 6-tert-butyl 3,6-diazabicyclo[3.2.0]heptane-3,6-dicarboxylate

799279-84-8
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3,6-Diazabicyclo[3.2.0]heptane-6-carboxylic acid, 1,1-diMethylethyl ester, (1R,5S)-

799279-81-5
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$239.00/250mg

Yield:799279-81-5 96%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20; for 10 h;

Steps:

8.B tert-Butyl(1R,5S)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate

Example 8B tert-Butyl(1R,5S)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate The product of Example 8A (40.0 g, 0.120 mol) was dissolved in methanol (400 mL) and treated with Pd/C (10 wt %, 4.0 g) under H₂ at ambient temperature for 10 h. The reaction was monitored with HPLC. After the reaction was complete, the catalyst was removed by filtration through a short column of diatomaceous earth. The filtrate was concentrated under reduced pressure to provide the title compound as a colorless oil (22.8 g, 11.5 mmol, 96% yield). ¹H NMR (MeOH-d₄, 300 MHz) δ 1.43 (s, 9H), 2.47 (dd, J=112.6, 3.8 Hz, 1H), 2.62 (dd, J=112.2, 5.7 Hz, 1H), 2.96 (m, 1H), 3.05 (d, J=112.2 Hz, 1H), 3.22 (d, J=112.5 Hz, 1H), 3.45 (m, 1H), 3.95 (m, 1H), 4.63 (dd, J=6.1, 3.7 Hz, 1H); MS (DCl/NH₃) m/z 199 (M+H)⁺. HPLC conditions: Zorbax-XDB-C8 column 4.6*250 mm with solvents H₂O (0.2 v.% HClO₄)/MeCN (from v.80:20 to 10:90 within 15 min.) at 1.0 mL/Min., UV detection ? 220 nm. 20/80, flow rate, 1.0 mL/min; uv 220 nm; t_R=8.6 minutes.

References:

US2005/101602,2005,A1 Location in patent:Page/Page column 30-31

370881-43-9 Synthesis

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

370881-43-9
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799279-81-5
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References

(3S,4S)-1-N-CBZ-3-(N-BOC-AMINO)-4-HYDROXYMETHYLPYRROLIDINE

246510-69-0
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799279-81-5
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benzyl 3-(tert-butoxycarbonylamino)-4-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

246510-70-3
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799279-81-5
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1-Pyrrolidinecarboxylic acid, 3-amino-4-[[(methylsulfonyl)oxy]methyl]-, phenylmethyl ester, (3S,4S)-, mono(trifluoroacetate) (9CI)

799279-83-7
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799279-81-5
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References