ChemicalBook CAS DataBase List (1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane

(1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane synthesis

3synthesis methods

Product Name:(1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane
CAS Number:370882-99-8
Molecular formula:C11H20N2O2
Molecular Weight:212.29

3,8-Diazabicyclo[4.2.0]octane-3-carboxylic acid, 8-[(1S)-1-phenylethyl]-, 1,1-dimethylethyl ester, (1R,6S)-

1295522-56-3
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(1R,6S)-3-Boc-3,8-diazabicyclo[4.2.0]octane

370882-99-8
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$60.00/5mg

Yield:370882-99-8 75%

Reaction Conditions:

with hydrogen;20% palladium hydroxide on carbon in ethanol;acetic acid at 50; under 75007.5 Torr; for 16 h;H-Cube;

Steps:

39

To a solution of (1 R,6S)-tert-butyl 8-((S)-1 -phenylethyl)-3,8- diazabicyclo[4.2.0]octane-3-carboxylate (1 .5 g, 75%) in EtOH (50 mL) was added AcOH (1 .5 mL). The resulting mixture was cycled through an H-Cube containing a 20% Pd(OH)₂/C catalyst cartridge at 50 °C and 100 bar of hydrogen pressure. After 16 hours the resulting mixture was removed from the H-Cube and poured over a saturated sodium carbonate solution (100 mL). The aqueous layer was extracted with DCM (50 mL) four times. The organic layers were combined, dried over Na₂SO₄, filtered and concentrated under reduced pressure to yield the title compound (755 mg, 75%) which was used in the next step without purification. MS (ESI) mass calcd. for C11 H20N2O2, 212.2; m/z found, 213.1 [M+H]⁺. ¹H NMR (500 MHz, CDCI₃): 4.21 - 4.02 (m, 1 H), 3.84 - 3.59 (m, 3H), 3.47 - 3.36 (m, 1 H), 3.33 (dd, J = 8.3, 4.4 Hz, 1 H), 3.28 - 3.20 (m, 1 H), 2.91 - 2.71 (m, 2H), 1 .94 - 1 .81 (m, 1 H), 1 .81 - 1 .68 (m, 1 H), 1 .46 (s, 9H).

References:

WO2011/50200,2011,A1 Location in patent:Page/Page column 69-70

3,8-Diazabicyclo[4.2.0]octane-3-carboxylic acid, 8-[(1R)-1-phenylethyl]-, 1,1-dimethylethyl ester, (1R,6S)-

923956-65-4
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370882-99-8
34 suppliers
$60.00/5mg

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3,8-Diazabicyclo[4.2.0]octane-3-carboxylic acid, 8-[(2-nitrophenyl)sulfonyl]-, 1,1-dimethylethyl ester, (1R,6S)-

370882-98-7
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370882-99-8
34 suppliers
$60.00/5mg

References