1-(tert-butyl) 3-methyl (3R,6R)-6-methylpiperidine-1,3-dicarboxylate synthesis

2synthesis methods

Product Name:1-(tert-butyl) 3-methyl (3R,6R)-6-methylpiperidine-1,3-dicarboxylate
CAS Number:1009376-92-4
Molecular formula:C13H23NO4
Molecular Weight:257.33

24424-99-5 Synthesis

24424-99-5
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1009376-88-8 Synthesis

(3R,6R)-methyl 6-methylpiperidine-3-carboxylate

1009376-88-8
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1-(tert-butyl) 3-methyl (3R,6R)-6-methylpiperidine-1,3-dicarboxylate

1009376-92-4
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Yield:1009376-92-4 93.4%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 1 h;Product distribution / selectivity;

Steps:

Preparation of (3R,6R)-1-tert-Butyl 3-Methyl 6-methylpiperidine-1,3-dicarboxylate (6-303α1-Me) To a solution of 6-313α1-Me (assumed 4.45 g) in CH₂Cl₂ (91 mL) and Et₃ N (16 mL, 4 equiv) was added 7.4 g (1.2 equiv) of Boc₂O at 0° C. After stirring at room temperature for 1 hour, GC-MS analysis indicated the reaction was complete. The reaction mixture was diluted with DI water (50 mL) and the phases were separated. The CH₂Cl₂ phase was dried (Na₂SO₄) and concentrated to a residue that was azeotroped with hexanes (2*250 mL) and purified by silica-gel column chromatography (99:1 n-heptane/ethyl acetate) to afford 6-303α1-Me (6.8 g, 93.4%).

References:

US2010/93706,2010,A1 Location in patent:Page/Page column 48

1-tert-butyl 3-methyl (3S,6R)-6-methylpiperidine-1,3-dicarboxylate

1009376-98-0
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1009376-92-4
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References