[ CAS No. 404577-34-0 ] {[proInfo.proName]}

Name: 404577-34-0|(R)-1-N-Boc-3-Methanesulfonyloxypiperidine|98%
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Quality Control of [ 404577-34-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 404577-34-0 ]

CAS No. :	404577-34-0	MDL No. :	MFCD09953026
Formula :	C₁₁H₂₁NO₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WLAZHMYDLUILKR-SECBINFHSA-N
M.W :	279.35	Pubchem ID :	29939737
Synonyms :

Safety of [ 404577-34-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 404577-34-0 ]

* 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.

Upstream synthesis route of [ 404577-34-0 ]
Downstream synthetic route of [ 404577-34-0 ]

[ 404577-34-0 ] Synthesis Path-Upstream 1~9

1
[ 404577-34-0 ]
[ 940890-90-4 ]

Reference： [1] Patent: CN103864673, 2016, B,

2
[ 124-63-0 ]
[ 143900-43-0 ]
[ 404577-34-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0 - 20℃; for 2.5 h;	B: (R)-3-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl Ester Methanesulfonyl chloride (1.73 ml, 22.5 mmol) was added to a cooled (ice bath, 0-4° C.), stirred solution of (R)-3-hydroxy-piperidine-carboxylic acid tert-butyl ester (3.0 g, 15 mmol) and triethylamine (3.12 ml, 22.5 mmol) in dichloromethane (30 ml). Following the addition the reaction was stirred at this temperature for 30 minutes before being allowed to warm to ambient temperature. After stirring at ambient temperature for 2 hours, aqueous sodium hydrogen carbonate (50 ml) was added, followed by vigorous stirring for 30 minutes. The reaction was diluted with dichloromethane (300 ml) and aqueous sodium hydrogen carbonate (300 ml) and after partitioning the organic phase was washed with water (200 ml), dried with magnesium sulphate and evaporated to dryness under reduced pressure to yield (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester as a semi-crystalline solid.24B: (R)-3-Methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester To a solution of (R)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (6.51 g, 32.3 mmol) and triethylamine (6.8 ml, 1.5 mol eq) in dichloromethane (70 ml) at 0° C. was added a solution of methanesulphonyl chloride (3.73 ml, 1.5 mol) in dichloromethane (30 ml) over 30 minutes. The reaction was stirred at 0° C. for 2 hours. Saturated sodium hydrogen carbonate (100 ml) was added slowly. The organic phase was separated, washed with brine and dried over magnesium sulphate. Evaporation under reduced pressure yielded (R)-3-methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester, 9.03 g (100percent). NMR (CDCl₃7.27d) m 4.73(1H), m 3.63d(2H), m 3.44d(1H), m 3.32d (1H), s 3.05d(3H), m 1.95d(2H), m 1.83d(1 H), m 1.54d(1H), s 1.46d(9H)
100%	With triethylamine In dichloromethane at 0℃; for 2 h;	24B: (f?)-3-Methanesulphonyloxypiperidine-1-carboxylic acid fe/f-butyl ester To a solution of (f?)-3-hydroxypiperidine-1-carboxylic acid terf-butyl ester (6.51 g,32.3 mmol) and triethylamine (6.8ml, 1.5 mol eq) in dichloromethane (70ml) at 0 0C was added a solution of methanesulphonyl chloride (3.73 ml, 1.5 mol) in dichloromethane (30 ml) over 30 minutes. The reaction was stirred at 0 0C for 2 hours. Saturated sodium hydrogen carbonate (100 ml) was added slowly. The organic phase was separated, washed with brine and dried over magnesium sulphate. Evaporation under reduced pressure yielded (f?)-3-methanesulphonyloxypiperidine-1-carboxylic acid terf-butyl ester,9.03g (100percent). NMR (CDCI3 7.27d) m 4.73/(1 H), m 3.63/(2H), m 3.44/(1 H), m 3.32/(1 H), s 3.05/(3H), m 1.95/(2H), m 1.83/(1 H), m 1.54/(1 H), s 1.46/(9H)
97%	With triethylamine In dichloromethane at 20℃; for 2 h;	To a solution of (R)-tert-butyl 3-hydroxypiperidine-1 -carboxylate (800 mg, 4.00 mmol) andTEA (2.02 g, 20.0 mmcl) in DCM (10 mL) was added MsCl (590 mg, 5.20 mmol) at 0 °C. Thesolution was warmed to room temperature and stirred for 2 hrs. The mixture was washed with H20 (10 mL x 2) and brine (20 mL), dried over Na2SO4 and concentrated to give the desired product (1.08 g, yield 97percent) as a yellow solid.1H NMR (300 MHz, CDCI3): ö 4.70 (brs, 1H), 3.75-3.60 (m, 2H), 3.47-3.39 (m, 1H), 3.35-3.27 (m, 1 H), 3.04 (s, 3H), 2.00-1.75 (m, 3H), 1.54-1.45 (m, 1 H), 1.45 (s, 9H).

95%

With triethylamine In dichloromethane at 0 - 20℃; for 1 h;

500ml three-necked flask, (R) -1-tert-butoxycarbonyl-3-hydroxypiper prepared in Example 6 (30.2 g, 0.15 mol) was added, 180 ml of methylene chloride, triethylamine (18.2 g; 0.18 mol) 0 to 10 ° C, methanesulfonyl chloride (18.9 g, 0.165 mol) was added dropwise, and the mixture was stirred at room temperature for 1 hour.The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated to give (R) -1-t-butoxycarbonyl methanesulfonic acid piperidine (39.8 g). (Yield: 95percent; LC-MS: m / e = 279.1) (Theory:41.9 g).

Reference： [1] Patent: US2007/135479, 2007, A1, . Location in patent: Page/Page column 6; 13
[2] Patent: WO2007/65916, 2007, A1, . Location in patent: Page/Page column 29
[3] MedChemComm, 2014, vol. 5, # 12, p. 1879 - 1886
[4] Patent: WO2017/12576, 2017, A1, . Location in patent: Page/Page column 185
[5] Patent: CN103864673, 2016, B, . Location in patent: Paragraph 0073-0075
[6] Patent: WO2007/65916, 2007, A1, . Location in patent: Page/Page column 13-14
[7] Patent: US2007/249672, 2007, A1, . Location in patent: Page/Page column 10
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2215 - 2221
[9] Patent: WO2005/305, 2005, A1, . Location in patent: Page 59
[10] Patent: WO2005/20975, 2005, A2, . Location in patent: Page/Page column 235; 236
[11] Patent: WO2005/20976, 2005, A2, . Location in patent: Page/Page column 238-239
[12] Patent: WO2005/60949, 2005, A2, . Location in patent: Page/Page column 237-238
[13] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2742 - 2746

3
[ 143900-43-0 ]
[ 404577-34-0 ]

Reference： [1] Patent: EP1320525, 2004, B1,

4
[ 14813-01-5 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,
[2] Patent: CN103864673, 2016, B,
[3] Patent: CN103864673, 2016, B,
[4] Patent: CN103864673, 2016, B,
[5] Patent: CN103864673, 2016, B,
[6] Patent: CN103864673, 2016, B,

5
[ 24424-99-5 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,
[2] Patent: CN103864673, 2016, B,

6
[ 91599-81-4 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,
[2] Patent: CN103864673, 2016, B,

7
[ 143900-44-1 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,

8
[ 940890-90-4 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,

9
[ 91599-79-0 ]
[ 404577-34-0 ]

Reference： [1] Patent: CN103864673, 2016, B,

[ 404577-34-0 ] Synthesis Path-Downstream 1~48

1
[ 404577-34-0 ]
[ 954127-40-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of NaH (0.30 g) in THF (20 mL) was added Intermediate 1 (using Starting Material 1) (1.22 g) dropwise. After stirring for 1 hour, Intermediate 3 (1.41 g) in THF was added and the reaction heated to 80 C. and left overnight. The reaction mixture was cooled to room temperature then quenched with aqueous saturated NaHCO3 (50 mL). Reaction mixture was extracted with DCM (2×50 mL). Combined organics were washed with water (100 mL), dried (NaSO4) and concentrated. Residue columned (flash, 20% EtOAC/Hx, silica). Yield: 946.9 mg. 1H-NMR (CDCl3) delta 7.50 (d, J=7.9 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 3.82 (d, J=13.4 Hz, 1H), 3.55-3.45 (m, 1H), 3.00-2.80 (m, 2H).

Reference： [1]Patent: US2007/249672,2007,A1 .Location in patent: Page/Page column 10

2
[ 404577-34-0 ]
[ 372-20-3 ]
C₁₆H₂₂FNO₃ [ No CAS ]
C₁₆H₂₂FNO₃ [ No CAS ]
[ 85838-94-4 ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

3
[ 404577-34-0 ]
[ 372-20-3 ]
(R)-3-(3-fluoro-phenoxy)-piperidine [ No CAS ]
(S)-3-(3-fluoro-phenoxy)-piperidine [ No CAS ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

4
[ 404577-34-0 ]
[ 108-39-4 ]
C₁₇H₂₅NO₃ [ No CAS ]
[ 85838-94-4 ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

5
[ 404577-34-0 ]
[ 108-39-4 ]
(S)-3-m-tolyloxy-piperidine [ No CAS ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

6
[ 124-63-0 ]
[ 143900-43-0 ]
[ 404577-34-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2.5h;Product distribution / selectivity;	B: (R)-3-Methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl Ester Methanesulfonyl chloride (1.73 ml, 22.5 mmol) was added to a cooled (ice bath, 0-4 C.), stirred solution of (R)-3-hydroxy-piperidine-carboxylic acid tert-butyl ester (3.0 g, 15 mmol) and triethylamine (3.12 ml, 22.5 mmol) in dichloromethane (30 ml). Following the addition the reaction was stirred at this temperature for 30 minutes before being allowed to warm to ambient temperature. After stirring at ambient temperature for 2 hours, aqueous sodium hydrogen carbonate (50 ml) was added, followed by vigorous stirring for 30 minutes. The reaction was diluted with dichloromethane (300 ml) and aqueous sodium hydrogen carbonate (300 ml) and after partitioning the organic phase was washed with water (200 ml), dried with magnesium sulphate and evaporated to dryness under reduced pressure to yield (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester as a semi-crystalline solid.24B: (R)-3-Methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester To a solution of <strong>[143900-43-0](R)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester</strong> (6.51 g, 32.3 mmol) and triethylamine (6.8 ml, 1.5 mol eq) in dichloromethane (70 ml) at 0 C. was added a solution of methanesulphonyl chloride (3.73 ml, 1.5 mol) in dichloromethane (30 ml) over 30 minutes. The reaction was stirred at 0 C. for 2 hours. Saturated sodium hydrogen carbonate (100 ml) was added slowly. The organic phase was separated, washed with brine and dried over magnesium sulphate. Evaporation under reduced pressure yielded (R)-3-methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester, 9.03 g (100%). NMR (CDCl3 7.27d) m 4.73(1H), m 3.63d(2H), m 3.44d(1H), m 3.32d (1H), s 3.05d(3H), m 1.95d(2H), m 1.83d(1 H), m 1.54d(1H), s 1.46d(9H)
100%	With triethylamine; In dichloromethane; at 0℃; for 2h;	24B: (f?)-3-Methanesulphonyloxypiperidine-1-carboxylic acid fe/f-butyl ester To a solution of (f?)-3-hydroxypiperidine-1-carboxylic acid terf-butyl ester (6.51 g,32.3 mmol) and triethylamine (6.8ml, 1.5 mol eq) in dichloromethane (70ml) at 0 0C was added a solution of methanesulphonyl chloride (3.73 ml, 1.5 mol) in dichloromethane (30 ml) over 30 minutes. The reaction was stirred at 0 0C for 2 hours. Saturated sodium hydrogen carbonate (100 ml) was added slowly. The organic phase was separated, washed with brine and dried over magnesium sulphate. Evaporation under reduced pressure yielded (f?)-3-methanesulphonyloxypiperidine-1-carboxylic acid terf-butyl ester,9.03g (100%). NMR (CDCI3 7.27d) m 4.73/(1 H), m 3.63/(2H), m 3.44/(1 H), m 3.32/(1 H), s 3.05/(3H), m 1.95/(2H), m 1.83/(1 H), m 1.54/(1 H), s 1.46/(9H)
97%	With triethylamine; In dichloromethane; at 20℃; for 2h;	To a solution of (R)-tert-butyl 3-hydroxypiperidine-1 -carboxylate (800 mg, 4.00 mmol) andTEA (2.02 g, 20.0 mmcl) in DCM (10 mL) was added MsCl (590 mg, 5.20 mmol) at 0 C. Thesolution was warmed to room temperature and stirred for 2 hrs. The mixture was washed with H20 (10 mL x 2) and brine (20 mL), dried over Na2SO4 and concentrated to give the desired product (1.08 g, yield 97%) as a yellow solid.1H NMR (300 MHz, CDCI3): oe 4.70 (brs, 1H), 3.75-3.60 (m, 2H), 3.47-3.39 (m, 1H), 3.35-3.27 (m, 1 H), 3.04 (s, 3H), 2.00-1.75 (m, 3H), 1.54-1.45 (m, 1 H), 1.45 (s, 9H).

95%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	500ml three-necked flask, (R) -1-tert-butoxycarbonyl-3-hydroxypiper prepared in Example 6 (30.2 g, 0.15 mol) was added, 180 ml of methylene chloride, triethylamine (18.2 g; 0.18 mol) 0 to 10 C, methanesulfonyl chloride (18.9 g, 0.165 mol) was added dropwise, and the mixture was stirred at room temperature for 1 hour.The organic phase was washed with water, dried over anhydrous sodium sulfate, and concentrated to give (R) -1-t-butoxycarbonyl methanesulfonic acid piperidine (39.8 g). (Yield: 95%; LC-MS: m / e = 279.1) (Theory:41.9 g).
		B: (RKS-Methanesulfonyloxy-piperidine-i-carboxylic acid te/t-butyl ester Methanesulfonyl chloride (1.73ml, 22.5mmol) was added to a cooled (ice bath, 0-4 C), stirred solution of (/^-S-hydroxy-piperidine-carboxylic acid te/t-butyl ester (3.Og, 15mmol) and triethylamine (3.12ml, 22.5mmol) in dichloromethane (30ml). Following the addition the reaction was stirred at this temperature for 30 minutes before being allowed to warm to ambient temperature. After stirring at ambient temperature for 2 hours, aqueous sodium hydrogen carbonate (50ml) was added, followed by vigorous stirring for 30 minutes. The reaction was diluted with dichloromethane (300ml) and aqueous sodium hydrogen carbonate (300ml) and after partitioning the organic phase was washed with water (200ml), dried with magnesium sulphate and evaporated to dryness under reduced pressure to yield (f?)-3-methanesulfonyloxypiperidine-1-carboxylic acid te/t-butyl ester as a semi-crystalline solid.
	With triethylamine; In dichloromethane; at 0℃; for 1h;	To a solution of Intermediate 2 (1 g) in DCM (10 mL) was added Et3N (1.38 mL) followed by MsCl (0.46 mL) dropwise at 0 C. After stirring at 0 C. for 1 hour the reaction was warmed to room temperature, quenched with water (10 mL) and separated. The aqueous layer was extracted with DCM (2×20 mL). Combined organics were washed with water (40 mL), a spatula of silica added, dried (NaSO4) and concentrated. Yield: 1.4148 g. 1H-NMR (CDCl3) delta 4.71 (1H, br s), 3.62 (2H, br d), 3.49-3.27 (2H, m), 3.04 (3H, s), 2.01-1.76 (3H, m), 1.79-1.71 (2H, m), 1.55-1.45 (1H, m), 1.45 (9H, s).
	With triethylamine; In dichloromethane; at 0℃; for 3.16667h;	Methanesulfonyl chloride (9.56mL, 124mmol) was added dropwise over 10 minutes to a stirred solution of 1, 1-dimethylethyl (3R)-3-HYDROXYPIPERIDINE-1-CARBOXYLATE (20.7g, 103mmol) and triethylamine (21.5mL, 154mmol) in dichloromethane (300mL) at 0C. After stirring for 3 hour at 0C, the reaction was quenched by addition of water. The organic phase was washed with brine, dried (MGS04), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl ACETATE/CYCLOHEXANE (20: 80 to 50 : 50), to give the title compound as an oil.
	With triethylamine; In dichloromethane; at 0℃; for 3h;	Methanesulfonyl chloride (9. 56ML, 124MMOL) was added dropwise over 10 minutes to a stirred solution of 1, 1-dimethylethyl (3R)-3-HYDROXYPIPERIDINE-1-CARBOXYLATE (20.7g, 103MMOL) and triethylamine (21. 5mL, 154mmol) in dichloromethane (300mL) at 0C. After stirring for 3 hour at 0C, the reaction was quenched by addition of water. The organic phase was washed with brine, dried (MGS04), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (20: 80 to 50: 50), to give the title compound as an oil.
	With triethylamine; In dichloromethane; at 0℃; for 3.16667h;	Methanesulfonyl chloride (9.56mL, 124mmol) was added dropwise over 10 minutes to a stirred solution of 1,1-dimethylethyl (3R)-3-HYDROXYPIPERIDINE-1-CARBOXYLATE (20.7g, 103MMOL) and triethylamine (21. 5mL, 154MMOL) in dichloromethane (300mL) at 0C. After stirring for 3 hour at 0C, the reaction was quenched by addition of water. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (20: 80 to 50: 50), to give the title compound as an oil.
	With triethylamine; In dichloromethane; at 0℃; for 3.16667h;	Methanesulfonyl chloride (9.56mL, 124mmol) was added dropwise over 10 minutes to a stirred solution of 1,1-dimethylethyl (3R)-3-hydroxypiperidine-1-carboxylate (20.7g, 103mmol) and triethylamine (21.5mL, 154mmol) in dichloromethane (300mL) at 0C. After stirring for 3 hour at 0C, the reaction was quenched by addition of water. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (20: 80 to 50: 50), to give the title compound as an oil.
3.06 g	With triethylamine; In dichloromethane; at 0℃; for 3h;	A mixture oftert-butyl (R)-3-hydroxypiperidine-l-carboxylate (5.15 g, 25 mmol) and Et3N (7.6 g, 77 mmol) in DCM (50 mL) was stirred at 0 C, MsCl (5.8 g, 52 mmol) was added to solution in dropwise, keep stirred for 3 h. The solvent was washed by saturated aqueous NaHC03 (50 mL 2) then brine (50 mL), dried over Na2S04, purified by flash chromatography on silica gel (DCM: 100%) to afford product as yellow solid, 3.06 g. ESI-MS m/z 280 (MH)+.

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 6; 13
[2]Patent: WO2007/65916,2007,A1 .Location in patent: Page/Page column 29
[3]MedChemComm,2014,vol. 5,p. 1879 - 1886
[4]Patent: WO2017/12576,2017,A1 .Location in patent: Page/Page column 185
[5]Patent: CN103864673,2016,B .Location in patent: Paragraph 0073-0075
[6]Patent: WO2007/65916,2007,A1 .Location in patent: Page/Page column 13-14
[7]Patent: US2007/249672,2007,A1 .Location in patent: Page/Page column 10
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2215 - 2221
[9]Patent: WO2005/305,2005,A1 .Location in patent: Page 59
[10]Patent: WO2005/20975,2005,A2 .Location in patent: Page/Page column 235; 236
[11]Patent: WO2005/20976,2005,A2 .Location in patent: Page/Page column 238-239
[12]Patent: WO2005/60949,2005,A2 .Location in patent: Page/Page column 237-238
[13]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2742 - 2746
[14]Patent: WO2019/232053,2019,A1 .Location in patent: Paragraph 00365

7
[ 404577-34-0 ]
[ 1271240-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In DMF (N,N-dimethyl-formamide); at 70℃; for 48h;	Sodium azide (7.65g, 118mmol) was added to a solution of 1, 1-dimethylethyl (3R)-3- [(METHYLSULFONYL) OXY]-PIPERIDINE-L-CARBOXYLATE (21.9g, 78. 5MMOL) in dry dimethylformamide (120ML) and the resultant suspension heated at 70C for 48 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic phase was washed two further times with water, then brine. The organic extracts were dried (MGS04), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (10: 90 to 50 : 50), to give the title compound as an oil.
	With sodium azide; In DMF (N,N-dimethyl-formamide); at 70℃; for 48h;	Sodium azide (7.65g, 118MMOL) was added to a solution of 1,1-dimethylethyl (3R)-3- [(METHYLSULFONYL) OXY]-PIPERIDINE-1-CARBOXYLATE (21.9g, 78. 5MMOL) in dry dimethylformamide (120ML) and the resultant suspension heated at 70C for 48 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic phase was washed two further times with water, then brine. The organic extracts were dried (MGS04), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (10: 90 to 50: 50), to give the title compound as an oil.
	With sodium azide; In DMF (N,N-dimethyl-formamide); at 70℃; for 48h;	Sodium azide (7.65g, 118mmol) was added to a solution of 1, 1-dimethylethyl (3R)-3- [(methylsulfonyl) oxy]-piperidine-l-carboxylate (21.9g, 78. 5mmol) in dry dimethylformamide (120mL) and the resultant suspension heated at 70C for 48 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic phase was washed two further times with water, then brine. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/cyclohexane (10: 90 to 50: 50), to give the title compound as an oil.

Reference： [1]Patent: WO2005/305,2005,A1 .Location in patent: Page 59-60
[2]Patent: WO2005/20976,2005,A2 .Location in patent: Page/Page column 239
[3]Patent: WO2005/60949,2005,A2 .Location in patent: Page/Page column 238

8
[ 404577-34-0 ]
[ 1374353-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; In N,N-dimethyl-formamide; at 70℃; for 48h;	Sodium azide (7. 65G, 118MMOL) was added to a solution of 1,1-dimethylethyl (3R)-3- [(METHYLSULFONYL) OXYL-PIPERIDINE-L-CARBOXYLATE (21.9g, 78. 5MMOL) in dry DIMETHYLFORMAMIDE (120ML) and the resultant suspension heated at 70C for 48 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted into ethyl acetate. The organic phase was washed two further times with water, then brine. The organic extracts were dried (MGS04), filtered and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl ACETATE/CYCLOHEXANE (10: 90 to 50: 50), to give the title compound as an oil

Reference： [1]Patent: WO2005/20975,2005,A2 .Location in patent: Page/Page column 236

9
[ 404577-34-0 ]
[ 104-87-0 ]
6-[1-(4-Methylbenzyl)piperidin-4-yloxy]-2H-isoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		30A: 6-[1-(4-Methylbenzyl)piperidin-4-yloxy]-2H-isoquinolin-1-one Sodium triacetoxyborohydride (100 mg, 3.9 mol eq) was added to a solution of 6-(piperidin-4-yloxy)-2H-isoquinolin-1-one (30 mg, 0.12 mmol), acetic acid (2 drops) and 4-methylbenzaldehyde (50 mul or 50 mg) in N, N-dimethylformamide (700 mul) and shaken for 17 hours. The reaction was quenched with water and methanol and the product semi-purified using an SCX cartridge. The product was further purified by prep-HPLC to afford 6-[1-(4-Methylbenzyl)piperidin4-yloxy]-2H-isoquinolin-1-one: El-MS: m/z=349.4 [M+H]+.

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 16

10
[ 404577-34-0 ]
[ 266690-49-7 ]
[ 940890-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20℃; for 48.0833h;Product distribution / selectivity;	C: (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl Ester To a solution of (R)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (209 mg, 1.04 mmol), triphenylphosphine (327 mg, 1.249 mmol), 1-amino-isoquinolin-6-ol (200 mg, 1.249 mmol) in THF (4 ml) and DMF (394muL) at 0 C., under argon, was added dropwise diethylazodicarboxylate (197 mL) over 5 min. The mixture was then warmed to ambient temperature and stirred for 48 h. Water was then added and the mixture basified with dilute NaOH. The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) filtered and evaporated under reduced pressure to give a residue. Flash chromatography of the residue on silica (eluent: 2-10% methanol in dichloromethane with 1% aqueous ammonia) gave (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg), El-MS: m/z=344.1 [M+H]+.For an alternate procedure for the preparation of (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester, a suspension of 1-amino-6-hydroxyisoquinoline (0.8 g, 5.0 mmol), (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester (1.76 g) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (3.4 g, -2.2 mmol/g loading) in acetonitrile (10 ml) were heated at 160 C. over a period of 15 minutes using the microwave. The excess supported regent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by chromatography on silica (eluent: 2-10% methanol in ethyl acetate) to afford (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg), El-MS: m/z=344.1 [M+H]+.
	With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine bound on polystyrene; In acetonitrile; at 160℃; for 0.25h;Microwave;	For an alternate procedure for the preparation of (S)-3-(1-amino-isoquinolin-6- yloxy)piperidin-1-carboxylic acid te/t-butyl ester, a suspension of 1-amino-6- hydroxyisoquinoline (0.8g, ?.Ommol), (/^-S-methanesulfonyloxypiperidine-i-carboxylic acid te/t-butyl ester (1.76g) and 2-te/t-butylimino-2-diethylamino-1 ,3-dimethyl-perhydro-1 ,3,2-diazaphosphorine on polystyrene (3.4g, ~2.2mmol/g loading) in acetonitrile (10ml) were heated at 160 C over a period of 15 minutes using the microwave. The excess supported regent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by chromatography on silica (eluent: 2-10% methanol in ethyl acetate) to afford (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid te/t-butyl ester (72 mg), EI-MS: m/z = 344.1 [M+H]+.
	With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene; In acetonitrile; at 160℃; for 0.25h;Microwave irradiation;Product distribution / selectivity;	C: (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl Ester To a solution of (R)-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (209 mg, 1.04 mmol), triphenylphosphine (327 mg, 1.249 mmol), 1-amino-isoquinolin-6-ol (200 mg, 1.249 mmol) in THF (4 ml) and DMF (394muL) at 0 C., under argon, was added dropwise diethylazodicarboxylate (197 mL) over 5 min. The mixture was then warmed to ambient temperature and stirred for 48 h. Water was then added and the mixture basified with dilute NaOH. The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) filtered and evaporated under reduced pressure to give a residue. Flash chromatography of the residue on silica (eluent: 2-10% methanol in dichloromethane with 1% aqueous ammonia) gave (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg), El-MS: m/z=344.1 [M+H]+.For an alternate procedure for the preparation of (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester, a suspension of 1-amino-6-hydroxyisoquinoline (0.8 g, 5.0 mmol), (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester (1.76 g) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (3.4 g, -2.2 mmol/g loading) in acetonitrile (10 ml) were heated at 160 C. over a period of 15 minutes using the microwave. The excess supported regent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by chromatography on silica (eluent: 2-10% methanol in ethyl acetate) to afford (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg), El-MS: m/z=344.1 [M+H]+.

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 6-7
[2]Patent: WO2007/65916,2007,A1 .Location in patent: Page/Page column 14
[3]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 6-7

11
[ 404577-34-0 ]
[ 252061-78-2 ]
[ 940890-77-7 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3.75h;	24C: (S)-3-(Oxo-1,2- dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester 6-Hydroxy-2H-isoquinolin-1-one (2 g, 12.41 mmol) and potassium carbonate (3.43 g, 2 mol) were mixed with N, N-dimethylformamide (40 ml) at 100 C. A solution of (R)-3- methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester (5.2 g, 1.5 mol) in dimethylformamide (50 ml) was added dropwise over 15 minutes. The mixture was stirred at 100 C. for 3.5 hours and allowed to cool. The crude material was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with sodium hydroxide (2M) then brine and dried over magnesium sulphate. The residue was purified by flash chromatography on silica (eluent: 0-100% Heptane/Ethyl acetate followed by 5% 2M ammonia in methanol/ethyl acetate) to give (S)-3-(Oxo-1,2-dihydroisoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (1.25g, 29%), El-MS: m/z=345.3 [M+H]+
29%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 3.75h;	24C: (S)-3-(Oxo-1 ,2- dihvdroisoquinolin-6-yloxy)piperidine-1-carboxylic acid fe/f-butyl ester6-Hydroxy-2H-isoquinolin-1-one (2g, 12.41 mmol) and potassium carbonate (3.43g, 2 mol) were mixed with ?/, ?/-dimethylformamide (40ml) at 100 0C. A solution of {R)-3- methanesulphonyloxypiperidine-i-carboxylic acid te/t-butyl ester (5.2g, 1.5 mol) in dimethylformamide (50 ml) was added dropwise over 15 minutes. The mixture was stirred at 100 0C for 3.5 hours and allowed to cool. The crude material was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and washed with sodium hydroxide (2M) then brine and dried over magnesium sulphate. The residue was purified by flash chromatography on silica (eluent: 0-100% Heptane/Ethyl acetate followed by 5% 2M ammonia in methanol/ethyl acetate) to give (S)-3-(Oxo-1 ,2- dihydroisoquinolin-6-yloxy)-piperidine-1-carboxylic acid te/t-butyl ester (1.25g, 29%), El- MS: m/z = 345.3 [M+H]+.

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 13
[2]Patent: WO2007/65916,2007,A1 .Location in patent: Page/Page column 29-30

12
[ 404577-34-0 ]
[ 940890-85-7 ]
(S)-3-(4-methyl-1-oxo-1,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester. [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 16h;	D: (S)-4-Methyl-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one A suspension of 6-hydroxy-4-methyl-2H-isoquinolin-1-one (60 mg, 0.34 mmol) and potassium carbonate (70 mg, 0.51 mmol) in DMF (2.5 ml) was heated to 110 C. and a solution of (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester (138 mg, 0.51 mmol) in DMF (1.5 ml) was added dropwise. Heating was continued at 110 C. for 16 hours and the solvent removed in vacuo. The residue was taken up in chloroform/isopropanol (3:1) and washed with aqueous sodium hydrogen carbonate. The organics were collected through a hydrophobic frit and concentrated to afford crude (S)-3-(4-methyl-1-oxo-1,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester. The crude (S)-3-(4-Methyl-1-oxo-1,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester was dissolved in 2 ml of DCM and excess TFA added (0.2 ml). After stirring for 2 hours the solvent was removed under reduced pressure and the residue dissolved in methanol and partially purified by ion exchange chromatography. Further purification by prep-HPLC gave (S)-4-methyl-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one, El-MS: m/z=259.1 [M+H]+.
	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 16h;	D: (S)-4-Methyl-6-(piperidin-3-yloxy)-2/-/-isoquinolin-1-oneA suspension of 6-hydroxy-4-methyl-2H-isoquinolin-1-one (60 mg, 0.34 mmol) and potassium carbonate (70 mg, 0.51 mmol) in DMF (2.5 ml) was heated to 110 C and a solution of (f?)-3-methanesulfonyloxypiperidine-1-carboxylic acid te/t-butyl ester (138 mg, 0.51 mmol) in DMF (1.5 ml) was added dropwise. Heating was continued at 110 C for 16 hours and the solvent removed in vacuo. The residue was taken up in chloroform / isopropanol (3:1 ) and washed with aqueous sodium hydrogen carbonate. The organics were collected through a hydrophobic frit and concentrated to afford crude (S)-3-(4- methyl-1-oxo-1 ,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester.The crude (S)-3-(4-Methyl-1-oxo-1 ,2-dihydroisoquinolin-6-yloxy)piperidine-1-car- boxylic acid fe/t-butyl ester was dissolved in 2 ml of DCM and excess TFA added (0.2 ml). After stirring for 2 hours the solvent was removed under reduced pressure and the residue dissolved in methanol and partially purified by ion exchange chromatography. Further purification by prep-HPLC gave (S)-4-methyl-6-(piperidin-3-yloxy)-2/-/-isoquino- lin-1-one, EI-MS: m/z = 259.1 [M+H]+.

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 15
[2]Patent: WO2007/65916,2007,A1 .Location in patent: Page/Page column 35-36

13
[ 404577-34-0 ]
[ 940890-87-9 ]
C₁₉H₂₃BrN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 0.333333h;Microwave irradiation;	B: (S)-5-Bromo-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one 5-Bromo-1-chloro-6-hydroxyisoquinoline (108 mg, 0.42 mmol) was mixed with hydrochloric acid (5M, 2 ml) and heated under microwave conditions at 150 C. for 40 minutes. The cooled residue was mixed with methanol and azeotroped to dryness under reduced pressure to give 5-bromo-6-hydroxy-2H-isoquinolin-1-one El-MS: m/z=240 and 242[M+H]+. The crude 5-bromo-6-hydroxy-2H-isoquinolin-1-one (93 mg) was mixed with (R)-3-methanesulphonyloxypiperidine-1-carboxylic acid tert-butyl ester (500 mg, 4.3 mol eq), potassium carbonate (700 mg, 12 mol eq) and N, N-dimethylformamide (2 ml). The mixture was microwaved at 150 C. for 20 minutes. Water was added to the mixture and the crude product extracted out into ethyl acetate. The organic phase was washed with brine and dried (MgSO4). The organics were concentrated in vacuo then purified by prep-HPLC. Dichloromethane and trifluoroacetic acid (3:1, 2 ml) were added and the mixture stirred for 1 h then concentrated in vacuo to give a residue. The residue was loaded onto a pre-acidified SCX column using methanol and eluted with 2M ammonia in methanol to afford (S)-5-bromo-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one. The residue was purified by prep-HPLC (1.8 mg), El-MS: m/z=323.5 and 323.5 [M+H]+

Reference： [1]Patent: US2007/135479,2007,A1 .Location in patent: Page/Page column 15-16

14
[ 143900-43-0 ]
[ 404577-34-0 ]
14-O-[(N-(3-Methyl-2-amino-buturyl-piperidin-3-yl)sulfanyl)acetyl]mutilin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; dichloromethane;	D) N-BOC-3(R)-methylsulfonyloxy-piperidine A solution of 5.08 g of N-BOC-3(R)-Hydroxy-piperidine and 8.7 g of methanesulfonic acid anhydride in 100 ml of pyridine is stirred at room temperature. Pyridine is distilled off under high vacuum and the distillation residue obtained is dissolved in CH2Cl2, which is extracted with 1N HCl. The organic phase obtained is dried and the solvent is evaporated off to dryness. The residue is purified by chromatography. 3.8 g of N-BOC-3(R)-methylsulfonyloxy-piperidine are obtained. 1H-NMR(CDCl3): 4.7(m,1H,CHOSO2CH3), 3.2-3.6(m,4H,CHN), 3.0(s,3H,CH3SO2), 1.4(m,9H,tert.butyl).

Reference： [1]Patent: EP1320525,2004,B1

15
[ 404577-34-0 ]
[ 39512-49-7 ]
(3'S)-4-(4-chlorophenyl)-1,3'-bipiperidin-4-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2215 - 2221

16
[ 404577-34-0 ]
[ 10387-40-3 ]
[ 610286-35-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2742 - 2746

17
[ 404577-34-0 ]
[ 266690-49-7 ]
[ 1268605-42-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 97 - 101

18
[ 404577-34-0 ]
[ 252061-78-2 ]
C₁₉H₂₄N₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1084 - 1088

Yield	Reaction Conditions	Operation in experiment
		General procedure: 1-(Methylsulfonyl)azetidin-3-yl methanesulfonate Azetidin-3-ol (3.3 g) and DIPEA (20 mL) are dissolved in dry tetrahydrofuran (40 mL). After 30 min the reaction mixture is cooled to 0 C. and methanesulfonyl chloride (10.9 g) is added dropwise. After stirring for 2 hours at ambient temperature, the mixture is concentrated under vacuum, partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. Chromatography of the residue on silica gel (cyclohexane/ethyl acetate 70:30) gives the title compound. Yield: 5 g. The intermediates in the following table are prepared following a procedure analogous to that described for Intermediate 26-4.

20
[ 143900-44-1 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

21
[ 24424-99-5 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B
[2]Patent: CN103864673,2016,B

22
[ 404577-34-0 ]
[ 143900-44-1 ]

Reference： [1]Patent: CN103864673,2016,B

23
[ 404577-34-0 ]
(R)-1-tert-butoxycarbonyl-3-p-nitrobenzenesulfonyloxypiperidine [ No CAS ]

Reference： [1]Patent: CN103864673,2016,B

24
[ 404577-34-0 ]
tert-butyl 3-(p-tolylsulfonyloxy)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: CN103864673,2016,B

25
[ 404577-34-0 ]
[ 940890-90-4 ]

Reference： [1]Patent: CN103864673,2016,B

26
[ 404577-34-0 ]
(S)-1-t-butoxycarbonyl-3-benzoyloxypiperidine [ No CAS ]

Reference： [1]Patent: CN103864673,2016,B
[2]Patent: CN103864673,2016,B

27
[ 404577-34-0 ]
tert-butyl (3R)-3-acetoxypiperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: CN103864673,2016,B

28
[ 404577-34-0 ]
[ 143900-43-0 ]

Reference： [1]Patent: CN103864673,2016,B

29
[ 404577-34-0 ]
[ 127-09-3 ]
(S)-1-tert-butoxycarbonyl-3-acetoxypiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 60℃;	To the 500ml three necked flask, (R) -1-t-butoxycarbonyl-3-methanesulfonopiperidine prepared in (1) or (2) of Example 7, (27.9 g, 0.1 mol), DMF 100 ml, sodium acetate (16.4 g;0.2mol), reaction at 60 overnight, quenched with water, extracted with ethyl acetate, washed with organic phase, concentrated(S) -1-tert-butoxycarbonyl-3-acetoxypiperidine crude. (Yield: ~ 100%; LC-MS: m / e= 243.3) (theory: 24.3 g).

Reference： [1]Patent: CN103864673,2016,B .Location in patent: Paragraph 0086-0088

30
[ 532-32-1 ]
[ 404577-34-0 ]
(S)-1-t-butoxycarbonyl-3-benzoyloxypiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 80℃;	(R) -1-tert-butoxycarbonyl-3-methanesulfonylpiperidine (27.9 g, 0.1 mol) prepared in (1) or (2) in Example 7 was added to a 500 ml three-necked flask DMF 100ml, sodium benzoate (28.8g; 0.2mol), 80 C reaction overnight, the reaction solution cooling, add Water quenched, extracted with dichloromethane, washed with organic phase and concentrated to give crude (S) -1-tert-butoxycarbonyl-3-benzoyloxypiperidine.. (Yield: ~ 100%; LC-MS: m / e= 243.3) (theory: 24.3 g).

Reference： [1]Patent: CN103864673,2016,B .Location in patent: Paragraph 0089-0091

31
[ 14813-01-5 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B
[2]Patent: CN103864673,2016,B
[3]Patent: CN103864673,2016,B
[4]Patent: CN103864673,2016,B
[5]Patent: CN103864673,2016,B
[6]Patent: CN103864673,2016,B

32
[ 940890-90-4 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

33
(S)-1-benzyl-3-piperidinyl benzoate [ No CAS ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

34
tert-butyl (3R)-3-acetoxypiperidine-1-carboxylate [ No CAS ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

35
(S)-1-benzyl-3-hydroxypiperidine camphorsulfonate [ No CAS ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

36
(R)-1-benzyl-3-hydroxypiperidine camphorsulfonate [ No CAS ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B
[2]Patent: CN103864673,2016,B

37
[ 91599-79-0 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B

38
[ 91599-81-4 ]
[ 404577-34-0 ]

Reference： [1]Patent: CN103864673,2016,B
[2]Patent: CN103864673,2016,B

39
[ 404577-34-0 ]
(S)-3-((benzyloxy)methyl)-5-methyl-1-(piperidin-3-yl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5172 - 5182

40
[ 404577-34-0 ]
C₃₁H₃₃N₃O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5172 - 5182

41
[ 404577-34-0 ]
C₃₁H₃₃N₃O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5172 - 5182

42
[ 404577-34-0 ]
[ 119451-90-0 ]
C₂₃H₃₁N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 96h;Inert atmosphere;	General procedure: A suspension of 3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione (20, 1.06 g, 4.3 mmol), tert-butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate (21, 1.80 g, 6.45 mmol) and potassium carbonate (1.19 g, 8.6 mmol) in dry DMF (10 mL) was stirred at 80 C for 48 h under argon. Additional 21 (1.20 g, 4.3 mmol) and potassium carbonate (0.60 g, 4.3 mmol) were added to the reaction mixture and the mixture was stirred at 80 C for 24 h. Additional 21 (1.20 g, 4.3 mmol) and potassium carbonate (0.60 g, 4.3 mmol) were added and the mixture was stirred at 80 C another 24 h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (100 mL), followed by washing with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate. After evaporation, the residue was purified by column chromatography (50% hexane/ethyl acetate) to give the intermediate which was dissolved with CH2Cl2 (20 mL), and TFA (2 mL) was added to the solution. The reaction mixture was stirred at room temperature for 3 h, followed by evaporation in vacuo. The residue was dissolved in sat. NaHCO3 solution (30 mL) and extracted with CH2Cl2 (50 mL × 3). The combined organic layers were washed with brine (50 mL × 2) and dried over sodium sulfate. The water layer can be re-extracted again if the product is found by TLC. After evaporation, the residue was purified by column chromatography (0.1% Et3N/4%MeOH/CH2Cl2) to afford the desired product 34 as colorless gel (0.60 g, 42.4%).

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5172 - 5182

43
[ 404577-34-0 ]
5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ol [ No CAS ]
(3S)-tert-butyl 3-((5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)oxy)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%		A mixture of 5-methyl-i -(tetrahydro-2H-pyran-2-yl)-1 H-indazol-6-oI (560 mg, 2.42 mmol) andCs2CO3 (2.36 g, 7.26 mmol) in CH3CN (20 mL) was stirred at 80 C for 15 mm. Then asolution of (R)-tert-butyl 3-((methylsulfonyl)oxy)piperidine-1 -carboxylate (1.08 g, 3.87 mmol)in CH3CN (10 mL) was added dropwise. The resulting mixture was stirred in reflux overnight.After cooled the mixture was concentrated. The mixture was partitioned with H20 (20 mL) and EtOAc (30 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica column (PE: EtOAc = 6:1)to give the desired product (0.18 g, yield 18%) as a yellow solid.1H NMR (300 MHz, CDCI3): O 7.84 (s, IH), 7.42 (ST IH), 7.01-6.85 (m, 1H), 5.66-5.63 (m,1H), 4.42 (br s, 1H), 4.03-3.90 (m, 1H), 3.77-3.64 (m, 1H), 3.62-3.21 (m, 3H), 2.63-2.52 (m,1H), 2.25 (s, 3H), 2.20-2.14 (m, 1H), 2.10-1.85 (m, 5H), 1.81-1.62 (m, 4H), 1.38-1.21 (m, 9H).

Reference： [1]Patent: WO2017/12576,2017,A1 .Location in patent: Page/Page column 185; 186

44
[ 404577-34-0 ]
(S)-4-(2-methoxy-6-(5-methyl-6-((1-methylpiperidin-3-yl)oxy)-1H-indazol-1-yl)pyrimidin-4-yl)morpholine [ No CAS ]

Reference： [1]Patent: WO2017/12576,2017,A1

45
[ 404577-34-0 ]
(S)-5-methyl-6-((1-methylpiperidin-3-yl)oxy)-1H-indazole [ No CAS ]

Reference： [1]Patent: WO2017/12576,2017,A1

46
[ 404577-34-0 ]
N-[3-[2-(difluoromethoxy)-5-(methylsulfanyl)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
tert-butyl (3S)-3-[3-[2-(difluoromethoxy)-5-(methylsulfanyl)phenyl]-4-[pyrazolo[1,5-a]pyrimidine-3-amido]-1H-pyrazol-1-yl]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃;	(S)-N-(3-(2-(difluoromethoxy)-5-(methylthio)phenyl)-l-(l-methylpiperidin-3-yl)-lH- pyrazol-4-yl)pyrazolo[ 1 ,5-a]pyrimidine-3-carboxamide To a mixture of Cs2C03(1.93 g, 5.92 mmol), N-[3-[2-(difluoromethoxy)-5- (methylsulfanyl)phenyl]-lH-pyrazol-4-yl]pyrazolo[l,5-a]pyrimidine-3-carboxamide (820 mg, 1.97 mmol) in DMF (12 mL) was added tert-butyl (3R)-3-(methanesulfonyloxy)piperidine-l- carboxylate (1.10 g, 3.94 mmol). The resulting solution was stirred at 60C overnight at 60C and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (3/2) and ethyl acetate. The appropriate fractions were combined and concentrated under vacuum. This resulted in 330 mg (24%) of tert-butyl 3-[3-[2-(difluoromethoxy)-5-(methylsulfanyl)phenyl]-4-[pyrazolo[l,5-a]pyrimidine-3-amido]-lH- pyrazol-l-yl]piperidine-l-carboxylate as light yellow oil. TLC: ethyl acetate, Rf= 0.4.

Reference： [1]Patent: WO2017/89390,2017,A1 .Location in patent: Page/Page column 90; 91

47
[ 288-13-1 ]
[ 404577-34-0 ]
(S)-tert-butyl 3-(1H-pyrazol-1-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.23%		To a solution of 60% NaH in mineral oil (20.04 g, 501 mmol) in N,N-dimethylformamide(DMF)(250 ml), at 0C was added 1 H-pyrazole (34.1 g, 501 mmol) in N,N-5 dimethylformamide(DMF) (250 ml) dropwise over a period of 30 min and stirred for 30 minat the same temperature. <strong>[404577-34-0](R)-tert-butyl 3-((methylsulfonyl)oxy)piperidine-1-carboxylate</strong> (70g,251 mmol) in N,N-dimethylformamide (DMF) (250 ml), was then added at 0C dropwisefor 30 min and then stirred for 30 min at 0C. The reaction mixture was heated to 50Cand stirred overnight. The reaction mixture was cooled to 0C, quenched with ice cold10 water and extracted with EtOAc (2 X 10000 ml). The organic layer was washed with coldwater (2 X 500ml), dried over anhydrous Na2S04, evaporated under reduced pressure.The residue was purified by flash chromatography, eluting with 0-5% EtOAc in petroleumether to provide the title compound. (14g, 55.7 mmol, 22.23% yield), LCMS m/z 252(M+Ht, 4.32 min (ret. time).

Reference： [1]Patent: WO2018/109643,2018,A1 .Location in patent: Page/Page column 100

48
[ 404577-34-0 ]
[ 10387-40-3 ]
[ 1402428-66-3 ]

Yield	Reaction Conditions	Operation in experiment
900 mg	In N,N-dimethyl-formamide; at 100 - 105℃; for 4h;Inert atmosphere;	A mixture oftert-butyl (R)-3-((methylsulfonyl)oxy)piperidine-l-carboxylate (3 g, 10.7 mmol) and KSAc (3.1 g, 26.8 mmol) was in DMF (30 mL) protected with N2. Warmed the solution to 100-105 C for 4 h. Cooled the solution to r.t.. Saturated aqueous NaHC03 (200 mL) was added to solution, extracted by DCM (100 mL 2). dired over Na2S04, purified by flash chromatography on silica gel (PE/EA=90/l0) to afford product as brown oil, 900 mg. ESI-MS m/z 260 (MH)+.

Reference： [1]Patent: WO2019/232053,2019,A1 .Location in patent: Paragraph 00365-00366

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H310	Fatal in contact with skin
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 404577-34-0 ] {[proInfo.proName]}

Quality Control of [ 404577-34-0 ]

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Product Details of [ 404577-34-0 ]

Safety of [ 404577-34-0 ]

Application In Synthesis of [ 404577-34-0 ]

[ 404577-34-0 ] Synthesis Path-Upstream 1~9

[ 404577-34-0 ] Synthesis Path-Downstream 1~48

Related Functional Groups of [ 404577-34-0 ]

Amides

Sulfonates

Related Parent Nucleus of [ 404577-34-0 ]

Piperidines

Precautionary Statements-General

Prevention

Response

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[ 404577-34-0 ]

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[ 404577-34-0 ]