Diisobutylaluminumhydride → [(R)-1-(4-Fluorophenyl)-6-[[6-(4-morpholinyl)-3-pyridinyl]sulfonyl]-1,4,7,8-tetrahydro-1,2,6-triazacyclopenta[b]naphthalen-4a-yl]methanol

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Reaction Steps

A solution of (R)-1-(4-fluorophenyl)-6-(6-morpholin-4-ylpyridine-3-sulfonyl)-1,4,5,6,7,8-hexahydro-1,2,6-triazacyclopenta[b]naphthalene-4a-carboxylic acid methyl ester (17 g) in dichloromethane (300 mL) under nitrogen at −78° C. was treated with a 1.0 M solution of diisobutylaluminium hydride in toluene (123 mL). After 1 hour at −78° C., the solution was diluted with water and the phases separated. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was triturated with diethyl ether to afford the title compound as a white solid (16.7 g). 1H NMR (CDCl3): δ 8.56-8.53 (d, 1H, J=2.4 Hz), 7.81-7.77 (dd, 1H, J=9.0, 2.4 Hz), 7.44-7.38 (m, 3H), 7.19-7.12 (m, 3H), 6.65-6.60 (d, 1H, J=9.0 Hz), 6.31-6.28 (d, 1H, J=2.5 Hz), 4.08-4.03 (dd, 1H, J=12, 2.4 Hz), 3.99-3.92 (m, 1H), 3.84-3.79 (m, 4H), 3.69-3.64 (m, 4H), 3.37-3.30 (m, 1H), 3.14-3.08 (d, 1H, J=16 Hz), 2.82-2.70 (m, 1H), 2.58-2.48 (m, 1H), 2.42-3.34 (m, 1H), 2.28-2.16 (m, 3H).

Provenance & Evidence