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Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 98 h; Stage #2: With hydrogenchloride In tetrahydrofuran
In two separate batches :- To a stirred solution of PI (380 g; 1.51 mol) in THF (3 1) at 0°C was added solid pellets of lithium aluminium hydride (229.4 g; 6.04 mol) over a period of 2 hours under nitrogen. The resulting grey suspension was allowed to warm to room temperature and stirred for 4 days after which HPLC showed no remaining starting material. The reaction mixture was diluted with THF (11), cooled to 0°C and solid sodium sulfate decahydrate was added over a period of 2 hours with rapid agitation. When the effervescence had subsided, the resulting suspension was filtered and the filtrate acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with THF (2 x 500 ml) and dried to a constant weight to afford Ml (batch 1: 86.8 g; 43percent) (batch 2: 97.3 g ; 49percent) as a white solid. The filter cakes obtained from the first filtration were suspended in 6N NaOH (400 ml) and filtered. The filtrate was extracted with diethyl ether (4 1). The organic layer was acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with diethyl ether (2 x 500 ml) and dried to a constant weight in a vacuum oven at 40°C to afford M I. HCI (105. 9 g) as a white solid. Yield: 72percent
72%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 98 h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In diethyl ether
In two separate batches: To a stirred solution of 26 (380 g; 1. 51 mol) in THF (3 1) at 0°C was added solid pellets of lithium aluminium hydride (229.4 g ; 6.04 mol) over a period of 2 hours under a blanket of nitrogen. The resulting grey suspension was allowed to warm to room temperature and stirred for 4 days after which HPLC showed no remaining starting material. The reaction mixture was diluted with THF (1 1), cooled to 0°C and solid sodium sulfate decahydrate was added over a period of 2 hours with rapid agitation. When the effervescence had subr sided, the resulting suspension was filtered and the filtrate acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with THF (2 x 500 ml) and dried to a constant weight to afford 108 (batch 1: 86.8 g; 43percent) (batch 2: 97.3 g; 49percent) as a white solid. The filter cakes obtained from the first filtration were suspended in 6N NaOH (400 ml) and filtered. The filtrate was extracted with diethyl ether (4 1). The organic layer was acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with diethyl ether (2 x 500 ml) and dried to a constant weight in a vacuum oven at 40°C to afford 27. HC1 (105.9 g) as a white solid. Yield: 72percent
72%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 98 h; Stage #2: With hydrogenchloride In tetrahydrofuran
In two separate batches :- To a stirred solution of PI (380 g; 1.51 mol) in THF (3 1) at 0°C was added solid pellets of lithium aluminium hydride (229.4 g; 6.04 mol) over a period of 2 hours under nitrogen. The resulting grey suspension was allowed to warm to room temperature and stirred for 4 days after which HPLC showed no remaining starting material. The reaction mixture was diluted with THF (11), cooled to 0°C and solid sodium sulfate decahydrate was added over a period of 2 hours with rapid agitation. When the effervescence had subsided, the resulting suspension was filtered and the filtrate acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with THF (2 x 500 ml) and dried to a constant weight to afford Ml (batch 1: 86.8 g; 43percent) (batch 2: 97.3 g ; 49percent) as a white solid. The filter cakes obtained from the first filtration were suspended in 6N NaOH (400 ml) and filtered. The filtrate was extracted with diethyl ether (4 1). The organic layer was acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with diethyl ether (2 x 500 ml) and dried to a constant weight in a vacuum oven at 40°C to afford M I. HCI (105. 9 g) as a white solid. Yield: 72percent
In two separate batches: To a stirred solution of 26 (380 g; 1. 51 mol) in THF (3 1) at 0C was added solid pellets of lithium aluminium hydride (229.4 g ; 6.04 mol) over a period of 2 hours under a blanket of nitrogen. The resulting grey suspension was allowed to warm to room temperature and stirred for 4 days after which HPLC showed no remaining starting material. The reaction mixture was diluted with THF (1 1), cooled to 0C and solid sodium sulfate decahydrate was added over a period of 2 hours with rapid agitation. When the effervescence had subr sided, the resulting suspension was filtered and the filtrate acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with THF (2 x 500 ml) and dried to a constant weight to afford 108 (batch 1: 86.8 g; 43%) (batch 2: 97.3 g; 49%) as a white solid. The filter cakes obtained from the first filtration were suspended in 6N NaOH (400 ml) and filtered. The filtrate was extracted with diethyl ether (4 1). The organic layer was acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with diethyl ether (2 x 500 ml) and dried to a constant weight in a vacuum oven at 40C to afford 27. HC1 (105.9 g) as a white solid. Yield: 72%
72%
In two separate batches :- To a stirred solution of PI (380 g; 1.51 mol) in THF (3 1) at 0C was added solid pellets of lithium aluminium hydride (229.4 g; 6.04 mol) over a period of 2 hours under nitrogen. The resulting grey suspension was allowed to warm to room temperature and stirred for 4 days after which HPLC showed no remaining starting material. The reaction mixture was diluted with THF (11), cooled to 0C and solid sodium sulfate decahydrate was added over a period of 2 hours with rapid agitation. When the effervescence had subsided, the resulting suspension was filtered and the filtrate acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with THF (2 x 500 ml) and dried to a constant weight to afford Ml (batch 1: 86.8 g; 43%) (batch 2: 97.3 g ; 49%) as a white solid. The filter cakes obtained from the first filtration were suspended in 6N NaOH (400 ml) and filtered. The filtrate was extracted with diethyl ether (4 1). The organic layer was acidified with gaseous HC1 affording a thick white precipitate which was collected by filtration, washed with diethyl ether (2 x 500 ml) and dried to a constant weight in a vacuum oven at 40C to afford M I. HCI (105. 9 g) as a white solid. Yield: 72%
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