(9H-fluoren-9-yl)methyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate hydrochloride synthesis

2synthesis methods

Product Name:(9H-fluoren-9-yl)methyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate hydrochloride
CAS Number:1445804-25-0
Molecular formula:C21H23ClN2O3
Molecular Weight:386.8719

3-Oxa-7,9-diazabicyclo[3.3.1]nonane-7,9-dicarboxylic acid, 7-(1,1-dimethylethyl) 9-(9H-fluoren-9-ylmethyl) ester

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(9H-fluoren-9-yl)methyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate hydrochloride

1445804-25-0
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Yield:1445804-25-0 92%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane at 20; for 1.5 h;

Steps:

Step 2 : 3-oxa-7.9-diaza-bicvclor3.3.11nonane-9-carboxylic acid 9H-fluoren-9-ylmethyl ester hydrochloride

3-Oxa-7,9-diaza-bicyclo[3.3.1]nonane-7,9-dicarboxylic acid 7-tert-butyl ester 9-(9H- fluoren-9-ylmethyl) ester (1.29 g, 2.76 mmol) was dissolved into a 4N solution of HCI in 1 ,4-dioxane (10 mL). The resulting mixture was stirred at RT for 1.5 hours, and then concentrated under vacuum to give a colorless oil. The oil was taken up with Et₂0 (20 ml) and a precipitation occurred. The precipitate was filtered off, washed with Et₂0 (2x) and dried under vacuum to give the title compound as a white powder (1.06 g, 92%). ¹H NMR (300 MHz, DMSO-d₆) δ 9.81 (s, 1 H), 8.22 (s, 1H), 7.90 (d, J = 7.3 Hz, 2H), 7.64 (d, J = 7.4 Hz, 2H), 7.47-7.31 (m, 4H), 4.61-4.44 (m, 2H), 4.31 (t, J = 6.0 Hz, 1 H), 4.07 (s, 1 H), 4.02-3.84 (m, 3H), 3.62-3.53 (m, 1 H), 3.51-3.37 (m, 3H), 3.09-2.90 (m, 2H). HPLC (max plot) 97.4%; Rt 2.94 min. UPLC/MS: (MS+) 351.3 ([M+H]⁺).

References:

WO2013/91773,2013,A1 Location in patent:Page/Page column 83

7-Boc-3-oxa-7,9-diazabicyclo[3.3.1]nonane

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82911-69-1 Synthesis

N-(9-Fluorenylmethoxycarbonyloxy)succinimide

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References