920297-39-8|1-(tert-Butoxycarbonyl)piperidine-3,5-dicarboxylic acid| Ambeed

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CAS No. :	920297-39-8
Formula :	C₁₂H₁₉NO₆
M.W :	273.28
SMILES Code :	O=C(C1CN(C(OC(C)(C)C)=O)CC(C(O)=O)C1)O
MDL No. :	MFCD24536044

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Yield	Reaction Conditions	Operation in experiment
80.9%		5) Dimethylpyridine-3,5-dicarbonate (100 g, 0.51 mol) and dimethylacetamide (400 mL) were charged in an autoclave (1 L), trifluoroacetic acid (59.2 mL, 0.77 mol) was added dropwise at 30 C. or lower, and 10% Pd-C (PE-type, 20.0 g) was added. The mixture was stirred at 55-65 C. for 12 hr under a hydrogen pressure (0.5-0.7 MPa). The catalyst was filtered off and the residue was washed with dimethylacetamide (50 mL2). The filtrates were combined, and triethylamine (77.8 g, 0.77 mol) was added dropwise at 20-30 C. to adjust the mixture to pH 9.0-10.0. Di-tert-butyl bicarbonate (134 g, 0.614 mol) was added dropwise at 30-40 C., and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was allowed to cool to 20-30 C., ethyl acetate (600 mL) was added, and the mixture was washed with water (900 mL). The aqueous layer was extracted again with ethyl acetate (400 mL). The organic layers were combined and washed successively with 5 w/v % citric acid-10 w/v % brine (600 mL), 3% sodium bicarbonate water (600 mL) and water (600 mL). The organic layer was concentrated under reduced pressure to the content (200 mL), methanol (250 mL) was added to the concentrated solution, and the mixture was concentrated under reduced pressure to the content (200 mL). Methanol (250 mL) was added again to the concentrated solution, the mixture was concentrated under reduced pressure to the content (200 mL), and methanol (2.40 L) was added. To this solution were added water (18.5 g, 1.03 mol) and cesium carbonate (417 g, 1.28 mol), and the mixture was stirred at 55-65 C. for about 24 hr. The reaction mixture was allowed to cool to 20-30 C. and concentrated to the content (700 mL), and tetrahydrofuran (500 mL) was added. To this solution was added dropwise 2N hydrochloric acid (1.28 L, 2.56 mol) at 15-35 C., and the mixture was adjusted to pH 3.0-3.5 and stirred at 20-30 C. for 30 min. The mixture was extracted with ethyl acetate (750 mL2), and the organic layer was washed with 10 w/v % brine (500 mL*3). The organic layer was concentrated under reduced pressure to the content (300 mL), and ethyl acetate was added to the content (650 mL). The concentrate was heated to 55-65 C., and heptane (500 mL) was added dropwise. The mixture was allowed to cool to 20-30 C. and stirred for 1 hr. The precipitated crystals were collected by filtration, washed with ethyl acetate-heptane (1:1, 120 mL), and dried under reduced pressure at 50 C. to give 1-(tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid as a white crystalline powder (113.3 g, yield 80.9%). 1H-NMR (300 MHz, DMSO-d6) delta 1.40 (s, 9H), 1.44-1.61 (m, 1H), 2.21-2.26 (m, 1H), 2.31-2.41 (m, 2H), 4.10-4.12 (m, 2H). Anal. Calcd for C12H19NO6: C, 52.74; H, 7.01; N, 5.13; O, 35.13. Found: C, 52.96; H, 6.99; N, 5.39.
1.21 g		To a solution of intermediate 2.147 (11.4 g, 58.3 mmol) in MeOH (58 mL) and 6 M aq. HCl (15 mL) was added rhodium on alumina (5%, 1.1 g). The resulting mixture was hydrogenated at 50 C while stirring under 200 bar pressure in a Parr reactor for 2 days. The reactor was then allowed to cool to room temperature and depressurized to ambient atmosphere. The crude heterogeneous resulting mixture was filtered through a bed of Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, and the resulting product was carried forward without additional purification. (0663) [00227] To a precooled (0 C) solution of crude intermediate (11.7 g, 58.3 mmol assumed) in CH2Cl2 (60 mL) under N2 atmosphere was added triethylamine (33 mL, 230 mmol) then Boc anhydride (20 mL, 87 mmol). The resulting mixture was then allowed to warm to room temperature and stirred for 16 h, then quenched with H2O. The layers were separated, and the aqueous phase was extracted with CH2Cl2 (3x). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography (SiO2, 75:25 hexanes:EtOAc, dry loaded Celite) afforded the product mixture as a clear colorless oil (3.08 g, 21% yield over 2 steps). The experimental data agreed with that in Imaeda, ACS Med. Chem. Lett.2016, 7 (10), 933-938; To a solution of intermediate 2.148 (3.00 g, 9.96 mmol) in MeOH (20 mL) at room temperature under N2 atmosphere was added 2 M aq. NaOH (10 mL, 20 mmol). The resulting mixture was stirred at room temperature for 18 h then concentrated in vacuo. The resulting residue was taken up in sat. aq. NaHCO3 and the aqueous layer was washed with ether (1x) then cooled to 0 C and acidified with 6 M aq. HCl to pH 2. The solid precipitate was collected by vacuum filtrated and dried to afford the product as a white solid (1.21 g, 45% yield). The experimental data agreed with that described in Imaeda, ACS Med. Chem. Lett.2016, 7 (10), 933-938. AMM 296.1117 (ESI) m/z [calc for C12H19NO6Na (M+Na)+ 296.1110].

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CAS No.: 920297-39-8

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CAS No.: 920297-39-8

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[ 920297-39-8 ] Synthesis Path-Downstream 1~1

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed