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Quality Control of 1-Boc-3-hydroxy-1,2,3,6-tetrahydropyridine Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of 1-Boc-3-hydroxy-1,2,3,6-tetrahydropyridine

CAS No. :	224779-27-5
Formula :	C₁₀H₁₇NO₃
M.W :	199.25
SMILES Code :	O=C(N1CC(O)C=CC1)OC(C)(C)C
MDL No. :	MFCD04972246
InChI Key :	NICJOYHYEDFTIX-UHFFFAOYSA-N
Pubchem ID :	17750131

Safety of 1-Boc-3-hydroxy-1,2,3,6-tetrahydropyridine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 1-Boc-3-hydroxy-1,2,3,6-tetrahydropyridine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 224779-27-5 ]

[ 224779-27-5 ] Synthesis Path-Downstream 1~35

1
[ 691-64-5 ]
1,2,3,6-Tetrahydro-pyridin-3-ol [ No CAS ]
[ 224779-27-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3589 - 3592.

2
[ 224779-27-5 ]
[ 156496-89-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With Dess-Martin periodane; In dichloromethane; for 3h;	To a solution of <strong>[224779-27-5]tert-butyl 3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate</strong> (CAS: 224779-27-5, 10 g, 50.19 mmol) in DCM (200 mL) was added Dess-Martin periodinane (25.55 g, 60.2 mmol). After stirring for 1.5 h additional amount of Dess-Martin periodinane (2.50 g, 12.54 mmol) was added together with DCM (50 mL). The reaction mixture was stirred for additional 1.5 h; then 750 mL of hexane was added and stirring was continued for 10 min. The solid that precipitated was filtered off. The filtrate was concentrated and treated with a fresh portion of hexane (500 mL), filtered and concentrated in vacuo to give 10.01 g (100%) of tert-butyl 3-oxo-3,6-dihydropyridine-1(2H)-carboxylate as a pale orange solid. ESI+MS: m/z=142.20 (M-56+1)+. 1H NMR (700 MHz, 300 K, DMSO-d6) delta 7.22 (bs, 1H), 6.10 (dt, J=10.3, 2.3 Hz, 1H), 4.18 (bs, 1H), 4.01 (bs, 1H), 1.42 (s, 9H).
98%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 2h;	Step 8) l-(tert-butoxycarbonyl)-L6-dihvdropyridin-3(2H)-one [0248] To a solution of l-(tert-butoxycarboxyl)-l,2,3,6-tetrahydropyridin-3-ol (350mg, 1.76 mmol) in DCM (12mL) was added Dess-Martin Oxidant (1.5 g, 3.52mmol). The reaction was stirred at rt for 2h, then filtered.The filtrate was washed with saturated aqueous a2CO3(50 mL), and concentrated in vacuo. The resulted residue was purified bya silica gel column chromatography (PE/EtOAc (v/v) =2/1) to give the title compound as colorless oil(340mg, 98%). LC-MS (ESI, pos. ion) m/z: 142[(M + H)+ - C4H8],220[M + Naf; 'tlNMR (400 MHz, CDC13) delta (ppm): 1.48(s, 9H), 4.11 (s, 2H), 4.24 (s, 2H), 6.16-6.20(m, 1H), 7.04 (s, 1H).
94%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 12h;	To a solution of l-(tert-butoxycarboxyl)-l,2,3 ,6-tetrahydropyridin-3-ol (300 mg, 1.50 mmol) in DCM (25 mL) was added Dess-Martin Oxidant (1.27 g, 3.00 mmol). The reactionsolution was stirred at RT for 12 hours and then filtered. The filtrate was washed with saturated aqueous Na2CO3 (50 mL) and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 2/1) to give the title compound as a colorless oil (280mg, yield 94%). MS (ES+) C10H15N03 requires: 197, found: 142 [M+H-56].

91%	With Dess-Martin periodane; In dichloromethane; at 20℃;	Example 10 Preparation of (E)-N-hydroxy-3-{4-[3-[(Z)-hydroxyimino]-5-(2-methyl-1H-indol-3-yl)-piperidin-1-ylmethyl]-phenyl}-acrylamide (8) To a solution of N-BOC-3-hydroxyl-1,2,3,6-tetrahydropyridine (0.988 g, 4.96 mmol) in dichloromethane (20 mL) is added Dess-Martin reagent (2.49 g, 5.69 mmol) and the resulting mixture is stirred at room temperature. After 2 h, the reaction mixture is treated with 20% aqueous sodium thiosulfate solution (40 mL) and extracted with ethyl acetate (370 mL). The combined organics are washed with a saturated aqueous solution of sodium bicarbonate (250 mL), brine (50 mL), dried over magnesium sulfate, filtered, and concentrated, and the residue is purified via a silica gel column chromatography to give 3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.890 g, 91% yield). LCMS (m/z): 198.1 (M+1).
91%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 2h;	To a solution ofN-BOC-3-hydroxyl- l ,2,3,6-tetrahydropyridine (0.988 g, 4.96 mmol) in dichloromethane (20 mL) is added Dess-Martin reagent (2.49 g, 5.69 mmol) and the resulting mixture is stirred at room temperature. After 2 h, the reaction mixture is treated with 20% aqueous sodium thiosulfate solution (40 mL) and extracted with ethyl acetate (3 x 70 mL). The combined organics are washed with a saturated aqueous solution of sodium bicarbonate(2 x 50 mL), brine (50 mL), dried over magnesium sulfate, fi ltered, and concentrated, and the residue is purified via a silica gel column chromatography to give 3-oxo-3,6-dihydro-2H- pyridine- l -carboxylic acid tert-butyl ester (0.890 g, 91 % yield). LCMS (m/z): 1 8. 1 (M+ l ).
61%	With pyridinium chlorochromate; In dichloromethane; for 1h;Inert atmosphere;	3-Hydroxy-3,6-dihydro-2H-pyridine- 1 -carboxylic acid tert-butyl ester (3.1 g, 17.3 mmol) was dissolved in dichloromethane (30 mL) under an argon atmosphere. Pyridinium chlorochromate (5 g, 23 mmol) was added in portions over 1 hour. The dichloromethane solution was filtered through silica gel (100 g), eluting withdichloromethane. The crude brown solid (2.84 g) was purified by MPLC (Companion) on a silica cartridge (40 g), eluting with 100% heptane followed by a gradient of ethyl acetate/heptane (0 to 60%). The product containing fractions were combined, concentrated, and dried under high vacuum for 1 hour at room temperature to provide 3- oxo-3,6-dihydro-2H-pyridine-l -carboxylic acid tert-butyl ester (2.1 g, 61% yield) as a clear oil that solidified on standing at low temperature. 1H NMR (300 MHz,CDCI3/TMS): delta = 6.95 (m, 1H), 6.08 (d, 1H, J= 10.5 Hz), 4.15 (m, 2H), 4.02 (br s, 2H), 1.39 (s, 9H). 13C NMR (75 MHz, CDCI3/TMS): delta = 193.11, 154.02, 147.17, 127.40, 80.89, 51.97, 42.69, 28.41.

References: [1]Patent: US2019/300525,2019,A1 .Location in patent: Paragraph 0294-0297; 0512-0514.
[2]Patent: WO2013/138210,2013,A1 .Location in patent: Paragraph 0248.
[3]Patent: WO2017/181117,2017,A1 .Location in patent: Page/Page column 240.
[4]Patent: US2011/53925,2011,A1 .Location in patent: Page/Page column 23.
[5]Patent: WO2012/25155,2012,A1 .Location in patent: Page/Page column 41.
[6]Synlett,2007,p. 741 - 744.
[7]Patent: WO2012/54535,2012,A2 .Location in patent: Page/Page column 178; 179.
[8]Tetrahedron Letters,1994,vol. 35,p. 3589 - 3592.

3
[ 36178-05-9 ]
[ 224779-27-5 ]
[ 564484-63-5 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 2995 - 2999.

4
[ 108-05-4 ]
[ 224779-27-5 ]
[ 780782-28-7 ]
[ 780782-21-0 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 5207 - 5214.
[2]Tetrahedron Letters,2004,vol. 45,p. 7053 - 7056.
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3558 - 3568.

5
[ 541-41-3 ]
[ 224779-27-5 ]
[ 224779-28-6 ]

References: [1]Journal of the American Chemical Society,2000,vol. 122,p. 7905 - 7920.

6
[ 224779-26-4 ]
[ 224779-27-5 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 5207 - 5214.
[2]Advanced Synthesis and Catalysis,2007,vol. 349,p. 685 - 693.
[3]Patent: WO2020/53600,2020,A1 .Location in patent: Page/Page column 22.
[4]Journal of the American Chemical Society,2000,vol. 122,p. 7905 - 7920.
[5]Synlett,2007,p. 741 - 744.

7
[ 24424-99-5 ]
[ 224779-27-5 ]
(+/-)-(3S,5S)-tert-butyl-2,4,5-trihydroxypiperidine-1-carboxylate [ No CAS ]
[ 858930-31-1 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 5207 - 5214.

8
[ 1666-17-7 ]
[ 224779-27-5 ]
C₂₄H₂₉N₃O₄S [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7113 - 7116.

9
[ 79-22-1 ]
[ 224779-27-5 ]
[ 656223-58-4 ]