 Home > Encyclopedia > TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE structure

CAS No:
885693-20-9
Formula:
C16H28BNO4
Chemical Name:
TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE
Synonyms:
TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE;1-Boc-3,6-dihydro-2H-pyridine-5-boronic acid pinacol ester;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;tert-butyl 5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate;1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-diMethylethyl ester;1-Boc-5,6-dihydro-2H-pyridine-3-boronic acid pinacol ester;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-but
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE Basic Attributes

Molecular Weight：

309.21

Exact Mass：

309.211151

DSSTox ID：

DTXSID70678619

HScode：

2934999090

Characteristics

PSA：

XLogP3：

3.12290

Density：

1.1±0.1 g/cm3

Boiling Point：

348°C at 760 mmHg

Flash Point：

164.3±30.7 °C

Refractive Index：

1.488

Safety Information

wgk germany：

GHS Classification：

|Warning|H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE Use and Manufacturing

PdClPdClb) PdClStep 2 To a solution of tert-butyl 3-(trifluoromethylsulfonyloxy)-5, 6-dihydropyridine- l(2H)- carboxylate (503-2) (1.4 g, 4.3 mmol), BPin ( 1.3 g, 5.1 mmol) and KOAc (1.26 g, 12.9 mmol) in dioxane (10 mL) was added Pd(dppf)ClTo a high pressure vessel was added 5-trifluoromethanesulfonyloxy-3, 6- dihydro-2H-pyridine- l-carboxylic acid tert-butyl ester (1.0 g, 3.0 mmol), dichloro[l , l '- bis(diphenylphosphino)ferrocene]palladium (II) acetone adduct (0.2 g, 0.3 mmol), Ι , - bis(diphenylphosphino)ferrocene (0.2 g, 0.3 mmol), bis(pinacolato)diboron (0.84 g, 3.3 mmol) and KA mixture of tert-butyl 5-(((trifluoromethyl)sulfonyl)oxy)-3, 6-dihydropyridine-1(2H)-carboxylate (3.5 g, 14.5 mmol), Pd(dppf)ClSilver oxide (0.098 g, .421 mmol), tert-butyl 3-(4, 4, 5, 5-tetramethyl- l, 3, 2-dioxaborolan-2-yl)-5, 6-dihydropyridine-l(2H)-carboxylate (0.052 g, .168 mmol), (2S , 3 S , 6R, 7S , 10R, E)- 10-hydroxy-2-((E)- 1 -iodoprop- 1 -en-2-yl)-3 , 7-dimethyl- 12- oxooxacyclododec-4-en-6-yl 4-methylpiperazine-l-carboxylate (007) (0.045g, 0.084 mmol), l, 4-dioxane (0.842 ml, 0.084 mmol), were combined and sparged with nitrogen for 10 minutes after which tetrakis(triphenylphosphine)palladium(0) (0.019 g, 0.017 mmol) was added and spargd with nitrogen for 10 minutes and stirred at 90 C for 1.5 hr. The reaction mix was filtered, concentrated and chromatographed to afford Example 219 (2S, 3S, 6R, 7S, l0R, E)-2-((E)-l-(l-(tert-butoxycarbonyl)-l, 2, 5, 6-tetrahydropyridin-3- yl)prop-l-en-2-yl)-l0-hydroxy-3, 7-dimethyl- l2-oxooxacyclododec-4-en-6-yl 4- methylpiperazine-l-carboxylate (12 mg, 0.020 mmol, 24.16 % yield).To a solution of tert- butyl 3-(4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)-5, 6 - dihydropyridine-1 (2/-/)-carboxylate (10.92 g, 35 mmol), 1 -bromo-3-methoxybenzene (6.6 g, 35 mmol) and Cs2C03 (3.44 g, 106 mmol) in 1 , 4-dioxane (50 ml.) and H20 (10 ml.) was added Pd(dppf)CI2 (1 .32 g, 1 .75 mmol). The reaction mixture was stirred overnight at 80 C. The solvent was removed. The residue was purified by column chromatography (petroleum ether/EtOAc = 10:1 ) to provide tert- butyl 3-(3-methoxyphenyl)-5, 6-dihydropyridine-1 {2H)- carboxylate. LC-MS (ESI): m/z 290.12 [M+H] +. 1 H NMR (400 MHz, CDCI3): d 7.26 (m, 1 H), 6.96 (m, 1 H), 6.89 (s, 1 H), 6.81 (m, 1 H), 6.19 (s, 1 H), 4.25 (s, 2H), 3.81 (s, 3H), 3.54 (m, 2H), 2.30 (s, 2H), 1 .49 (s, 9H).

Computed Properties

Molecular Weight:309.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:309.2111385
Monoisotopic Mass:309.2111385
Topological Polar Surface Area:48
Heavy Atom Count:22
Complexity:463
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
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TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE

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