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Stage #1: With mercury(II) diacetate In tetrahydrofuran; water for 3 h; Stage #2: With sodium hydroxide In tetrahydrofuran; water for 19 h;
Add 2-[benzyl-(2-methyl-allyl)-amino]-ethanol (13.0 g, 63.2 mmol) to a slurry of mercury (H) acetate (20.7 g, 65.0 mmol) in water (45 mL) and THF (45 mL). After 3 h, treat the mixture with NaOH (25 mL, 2.5 M aqueous, 125 mmol) followed by NaBH4 (2.72 g, 71.9 mmol). After 19 h, decant the mixture away from the metallic mercury and add to a separatory funnel with fert-butyl methyl ether (250 mL). Separate the organic solution, wash with water (250 mL), filter through a silica plug, and concentrate. Purify the residue by flash chromatography using a gradient from 5percent to 10percent tert-butyl methyl ether in CH2Cl2. Collect and concentrate the fractions containing product then dissolve the residue in hexanes (100 mL). Filter the solution through Celite.(R). to remove metallic mercury and then concentrate the filtrate to give the title compound (7.01g, 54percent) as a colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.20-7.40 (5H, m), 3.60 (2H, m), 3.42 (2H, s), 2.29 (2H. m), 2.10 (2H, s), 1.14 (6H, s).
Add 2-[benzyl-(2-methyl-allyl)-amino]-ethanol (13.0 g, 63.2 mmol) to a slurry of mercury (H) acetate (20.7 g, 65.0 mmol) in water (45 mL) and THF (45 mL). After 3 h, treat the mixture with NaOH (25 mL, 2.5 M aqueous, 125 mmol) followed by NaBH4 (2.72 g, 71.9 mmol). After 19 h, decant the mixture away from the metallic mercury and add to a separatory funnel with fert-butyl methyl ether (250 mL). Separate the organic solution, wash with water (250 mL), filter through a silica plug, and concentrate. Purify the residue by flash chromatography using a gradient from 5% to 10% tert-butyl methyl ether in CH2Cl2. Collect and concentrate the fractions containing product then dissolve the residue in hexanes (100 mL). Filter the solution through Celite to remove metallic mercury and then concentrate the filtrate to give the title compound (7.01g, 54%) as a colorless liquid. 1H NMR (DMSO-d6, 400 MHz) delta 7.20-7.40 (5H, m), 3.60 (2H, m), 3.42 (2H, s), 2.29 (2H. m), 2.10 (2H, s), 1.14 (6H, s).
In methanol; dichloromethane; at 20 - 60℃; for 6h;
Dissolve <strong>[84761-04-6]4-benzyl-2,2-dimethyl-morpholine</strong> (5.67 g, 27.6 mmol) in CH2Cl2 (50 mL) and add 1-chloroethyl chloroformate (4.60 mL, 42.2 mmol) while stirring at room temperature. After 4 h, concentrate the solution and treat the residue with MeOH (60 mL). Heat the mixture at 60 C for 2 h, then concentrate again. Dissolve the residue in water (125 mL) and wash with tert-butyl methyl ether (125 mL). Concentrate the aqueous EPO <DP n="134"/>layer and dry the resulting residue at 80 C under vacuum to give the title compound (3.91 g, 93%) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 9.52 (2H, br s), 3.75 (2H, m), 2.89-2.96 (4H, m), 1.25 (6H, s).
4-benzyl-2-(iodomethyl)-2-methylmorpholine[ No CAS ]
[ 84761-04-6 ]
Yield
Reaction Conditions
Operation in experiment
55.6%
With sodium tetrahydroborate; In dimethyl sulfoxide; at 100℃; for 4.5h;
NaBH4 (2.485 g, 65.7 mmol) was added to a solution of 1315B (14.5 g, 43.8 mmol) DMSO (75 mL) and then the reaction mixture was stirred and heated at 100 C., for 4.5 h. The reaction mixture was quenched with 5M HCl (50 ml) and stirred for 15 minutes. Then added 5M NaOH (50 mL) and 1M Na2S2O3 (100 mL) stirred the mixture for 6 h. The mixture diluted with water (100 mL) and extracted with tert-butyl methyl ether (2*250 mL). The organic layers were separated, washed with water (4*100 dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude, which was purified by flash silica gel column chromatography to afford 1317C (colorless liquid, 5.0 g, 24.36 mmol, 55.6% yield). LC-MS Anal. Calc'd. for C13H19NO, 205.2. found [M+H] 206.2, Tr=2.641 min (Method U).
1315C (2.5 g, 12.18 mmol) dissolved in DCM (25 mL), followed by addition of 1-chloroethyl chloroformate (2.61 g, 18.27 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure to afford the residue. The residue dissolved in MeOH (25 mL), heated at 60 C. and stirred for 2 h. The solvents were evaporated and the residue was dissolved in water (10 mL) and washed with tert-butyl methyl ether (25 mL). The aqueous layer concentrated under reduced pressure to afford the residue, dried at 80 C., under vacuum to give 1315D (white solid, 1.5 g, 9.89 mmol, 81% yield). 1H NMR (400 MHz, DMSO-d6) delta 9.51 (s, 2H), 3.74-3.82 (m, 2H), 2.91-2.95 (m, 4H), 1.25 (s, 6H).
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