反応 #42250

反応方程式

lithium aluminum hydride

(±)-methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate

hydrogen chloride

→

(±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)-N-methylmethanamine

収率 23.3%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他the resulting reaction mixture
2. 2
   その他quenched with saturated ammonium chloride (50 mL)
3. 3
   その他the organic layer was separated
4. 4
   洗浄washed with saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL)
5. 5
   乾燥dried (magnesium sulfate)
6. 6
   その他the solvent was removed in vacuo
7. 7
   その他to provide a crude oil
8. 8
   その他Purification by flash chromatography (silica, methanol:dichloromethane 1:39)
9. 9
   その他provided a light brown oil
10. 10
    ろ過The resulting precipitate was filtered
11. 11
    洗浄washed (diethyl ether)
12. 12
    その他dried

実験手順

To a suspension of lithium aluminum hydride (95 wt. %, 0.45 g, 11.25 mmol) in tetrahydrofuran (45 mL) was added (±)-methyl (5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)methylcarbamate (1.16 g, 3.98 mmol) and the resulting reaction mixture was allowed to stir at room temperature for 40 h. The reaction mixture was diluted with tetrahydrofuran (150 mL), quenched with saturated ammonium chloride (50 mL), and the organic layer was separated and washed with saturated aqueous sodium bicarbonate (50 mL), saturated aqueous sodium chloride (50 mL), dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash chromatography (silica, methanol:dichloromethane 1:39) provided a light brown oil. The oil was re-dissolved in tetrahydrofuran (50 mL) and aqueous hydrogen chloride (1.0 N, 1 mL) was added. The resulting precipitate was filtered, washed (diethyl ether), and dried to afford 0.23 g (20%) of (±)-1-(5-chloro-2,3-dihydronaphtho[1,2-b]furan-2-yl)-N-methylmethanamine as a white solid, hydrochloride salt. mp 224-226° C.; Anal. calcd. for C14H14ClNOHCl.0.1H2O: C, 58.80; H, 5.36; N, 4.90. Found: C, 58.65; H, 5.30; N, 4.84.

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