N[C@@H]1CCCC2C=C(CO)C=CC1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:31]2[CH:30]([N:34]=[N+:35]=[N-:36])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)=[O:23].[OH-].[Na+]>C1COCC1.O>[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:31]2[C@H:30]([N:34]=[N+:35]=[N-:36])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)=[O:23]
Preparation (5(R)-Amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol: To an oven-dried, 3-neck, 2 L round-bottomed flask equipped with argon inlet/outlet, addition funnel, thermometer, and overhead stirring was added 700 mL of THF and LAH (470 mL of a 1M soln in THF, 470 mmol, Aldrich). The reaction was cooled in a ice-salt bath, and 5-azido-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (27 g, 120 mmol) in 100 mL of THF was added over ca. 30 min. The mixture was warmed to RT overnight, then cooled in an ice-salt bath the next morning. Water (18 mL) in THF (20 mL) was added to the reaction mixture over 4 h. Vigorous gas evolution occurred. 5M NaOH (18 mL) was added over 30 min followed by 54 mL of water. After stirring for an additional 1 h, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was reconstituted in MeOH and CH3CN, and concentrated in vacuo again to provide the title compound as light-brown solid. MS (+ ion ESI) m/z=161 (M-NH3).
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