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Solid states of 5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene's intermediates

IP.com Disclosure Number: IPCOM000171516D
Publication Date: 2008-Jun-12

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The IP.com Prior Art Database

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1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diol

    1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diol described according to the following formula:

C11H12O2

Mw: 176 gr/mol

is an intermediate in the preparation process of 5,8,14- Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene.

    The following procedure provides a preparation process of 1,2,3,4- Tetrahydro-1,4-methano-napthalene-2,3-diol.

Preparation of 1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diol:

    In a 1L 4 neck round bottom flask equipped with mechanical stirrer, thermo pocket etc. were charged acetone 1000ml , N-methyl morpholine N-oxide (97.08 g) & 1,4-dihydro-1,4-methanonaphtalen-9-ylidene (100.0 gm), water (125.7 ml) at 25-300C& stirred. To this mixture was added 15 mole % solution of osmium tetroxide (0.233 gm) in n-butanol (6.05ml) at 25-300C.The reaction mixture was maintained at 25-300C for 50-60hrs.The solvent was distilled out under vacuum below 50oC, and to the residue charged acetone (250 ml) and stirred for 1.0hr at 25- 30 oC. Reaction mass was filtered & washed with acetone (150 ml),and air dried to obtain 1st crop of1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diol(63.31gm HPLC purity- NLT 99 %.).The mother liquor was concentrated to afford semi solid which was triturated with acetone (250 ml) and stirred for 1 hrs. The solid filtered and washed with acetone (150ml) and air dried to get 2nd crop of1,2,3,4- Tetrahydro-1, 4-methano-napthalene-2,3-diol(34.0 gm HPLC purity- NLT 99 %).

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    1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diol was analyzed by XRPD and its XRD peaks are presented in the X-ray diffractogram provided in pattern #1.

Pattern #1:

Main XRD peaks of 1,2,3,4-Tetrahydro-1,4-methano-napthalene-2,3-diolare: 5.8,
6.3, 9.5, 12.8, 16.0, 17.7, 19.3, 21.0, 23.1 and 32.5± 0.2 degrees 2-theta.

    The analysis was performed on Bruker X-Ray powder diffractometer model D8 advance equipped with lynxEye.

1, 2, 3, 4-Tetrahydro-1, 4-methano-napthalene-2, 3-diol was analyzed by FT-IR (KBr pellet) and its FT-IR peaks are presented in the spectrum provided in pattern #2.

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Pattern #2:

    Main FTIR peaks of 1, 2, 3, 4-Tetrahydro-1, 4-methano-napthalene-2, 3-diolare: 750, 1082, 1319, 1407, 1455, 1471, 1678, 2936, 3239, 3387 cm-1

The analysis was performed on NICOLET AVATAR 370DTGS.

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10-Benzyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene

    10-Benzyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene described according to the following formula:

C18H19N

Mw: 249 gr/mol

is an intermediate in the preparation process of 5,8,14- Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2(11),3,5,7,9-pentaene.

    The following procedure provides...