581060-27-7|1-Boc-4-(Mercaptomethyl)piperidine| Ambeed

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Quality Control of [ 581060-27-7 ] Purity: 97% SDS Specification

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Product Details of [ 581060-27-7 ]

CAS No. :	581060-27-7
Formula :	C₁₁H₂₁NO₂S
M.W :	231.36
SMILES Code :	SCC1CCN(C(OC(C)(C)C)=O)CC1
MDL No. :	MFCD19689418
InChI Key :	VEPAXJUGIFPJNK-UHFFFAOYSA-N
Pubchem ID :	58694772

Safety of [ 581060-27-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H319-H332-H372-H400
Precautionary Statements:	P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Application In Synthesis of [ 581060-27-7 ]

* 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 [ 581060-27-7 ]

[ 581060-27-7 ] Synthesis Path-Downstream 1~28

1
[ 581060-27-7 ]
[ 165197-50-2 ]
[ 165197-39-7 ]

References: [1]Journal of Antibiotics,1995,vol. 48,p. 408 - 416.

2
[ 718610-84-5 ]
[ 581060-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 2.16667h;	Step 2 Preparation OF N-BOC-PIPERIDIN-4-YHNETHYLTHIOL. Sodium borohydride (2.2 g) was added in portions over 10 minutes to a solution of (N- Boc-piperidin-4-yl) methylthioacetate (2.2 g) in methanol (40 ml) at 0C. The mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was evaporated and the residue was dissolved in water (10 ml), citric acid (2g) was added and the mixture was extracted with dichloromethane (3X20 ml) and dried. Removal of the solvent gave the product as an orange oil, which by NMR CONTAINED-29% of the starting material. This product was used without further purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 170 - 174.
[2]Patent: WO2004/56773,2004,A1 .Location in patent: Page 82.

3
[ 5349-17-7 ]
[ 581060-27-7 ]
4-(2-oxo-2-pyridin-4-ylethylsulfanylmethyl)piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In 1,4-dioxane; for 16h;	t-BuOK (44 mg, 400 mumol) was added to a stirred solution of 4-mercaptomethyl piperidine-1-carboxylic acid tert-butyl ester (Preparation 1, 50 mg, 216 mumol) and 2-bromo-l- pyridin-4-ylethanone hydrobromide (121 mg, 432 mumol) in anhydrous dioxane (3 mL). After 16 h, the reaction mixture was diluted with EtOAc (70 mL), before being washed with H2O (15 mL) and brine (15 mL). After drying (MgSO4), the organic phase was filtered, concentrated, and purified by column chromatography (IH-EtOAc, 1 : 1) to furnish the title compound: RT = 3.72 min; mlz (ES+) = 351.2 [M+ H]+.

References: [1]Patent: WO2006/67531,2006,A1 .Location in patent: Page/Page column 25.

4
4-carbamimidoylsulfanylmethylpiperidine-1-carboxylic acid tert-butyl ester tosylate [ No CAS ]
[ 581060-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; water; at 100℃; for 0.333333h;	Preparation 3; 4-Mercaptomethylpiperidine-l-carboxylic acid tert-butyl ester; A stirred solution of N-tert-butoxycarbonyl-4-(4-toluenesulfonyloxymethyl)piperidine (240 mg, 0.65 mmol) and thiourea (99 mg, 1.30 mmol) in EtOH (1 mL) was heated under gentle reflux for 16h. The solvent was evaporated off under reduced pressure to furnish the tosylate salt of 4-carbamimidoylsulfanylmethylpiperidine-l-carboxylic acid tert-butyl ester: m/z (ES+) = 274.0 [M+ H]+. A solution of this salt (250 mg, 0.56 mmol) in H2O (1 mL) and concentrated aqueous NH3 (2 mL) was heated to 1000C with stirring for 20 min. On cooling, the mixture was partitioned between Et2O (30 mL) and H2O (10 mL), the pH of the aqueous phase being adjusted to 7 using 2 M HCl and saturated aqueous NaHCO3. The organic phase was extracted with 1 M NaOH (15 mL), then the aqueous extracts were neutralised to pH 7 with 2 M HCl. The cloudy mixture was extracted with Et2O (50 mL), then the organic extracts were washed with brine (10 mL) and dried (MgSO4). Filtration and solvent evaporation furnished the title compound
		A stirred solution of N-tert-butoxycarbonyl-4-(4-toluenesulfonyloxymethyl)piperidine (240 mg, 0.65 mmol) and thiourea (99 mg, 1.30 mmol) in EtOH (1 mL) was heated under gentle reflux for 16 h. The solvent was evaporated off under reduced pressure to furnish the tosylate salt of 4-carbamimidoylsulfanylmethylpiperidine-l-carboxylic acid tert-butyl ester: m/z (ES+) = 274.0 [M+ H]+. A solution of this salt (250 mg, 0.56 mmol) in H2O (1 mL) and concentrated aqueous NH3 (2 mL) was heated to 100 0C with stirring for 20 min. On cooling, the mixture was partitioned between Et2O (30 mL) and H2O (10 mL). The pH of the aqueous phase was adjusted to 7 using 2 M HCl and saturated aqueous NaHCO3. The organic phase was extracted with 1 M NaOH (15 mL), then the aqueous extracts were neutralised to pH 7 with 2 M HCl. The cloudy mixture was extracted with Et2O (50 mL), then the organic extracts were washed with brine (10 mL) and dried (MgSO4). Filtration and solvent evaporation furnished the title compound: deltaH (CDCl3) 1.05-1.20 (m, 2H), 1.35 (t, IH), 1.48 (s, 9H), 1.50-1.60 (m, IH), 1.80-1.90 (m, 2H), 2.40-2.50 (m, 2H), 2.60-2.80 (m, 2H), 4.05^.25 (m, 2H).

References: [1]Patent: WO2006/67532,2006,A1 .Location in patent: Page/Page column 19.
[2]Patent: WO2006/67531,2006,A1 .Location in patent: Page/Page column 16.

5
[ 31716-01-5 ]
[ 581060-27-7 ]
[ 1184144-27-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 170 - 174.

6
[ 40517-43-9 ]
[ 581060-27-7 ]
[ 718610-85-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 3 Preparation of [ (N-BOC-PIPERIDIN-4-YL) METHYL]- (4-METHANESULPHONYL- PHENYLMETHYL) sulphide N-Boc-piperidin-4-ylmethylthiol (1.155 g) was added to a suspension of sodium hydride (200 mg of a 60% dispersion in mineral oil) in DMF at 0C and the mixture was stirred for 30 minutes. 4-METHANESULPHONYLBENZYL chloride (1.023 g) was added, the reaction mixture was allowed to warm to room temperature and was stirred for 1 hour. The reaction mixture was evaporated to dryness and the residue was dissolved in dichloromethane (30 ml) and washed with water (25 ml) and brine (25 ml) and dried. The solvent was evaporated and the residue was purified on a 50g silica Bond Elut eluting with a solvent gradient (isohexane- 50% ethyl ACETATE/ISOHEXANE). Yield LG, MH 300. NMR (CDC13) : 1.2 (m, 2H), 1.45 (s, 9H), 1.5 (m, 1H), 1.8 (m, 2H), 2.35 (d, 2H), 2.65 (bt, 2H), 3.05 (s, 3H), 3.75 (s, 3H), 4.1 (m, 2H), 7.5 (d, 2H), 7.9 (d, 2H).

References: [1]Patent: WO2004/56773,2004,A1 .Location in patent: Page 82.

8
[ 1236007-02-5 ]
[ 581060-27-7 ]
[ 1236007-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 130℃; for 18h;	Example 20[0439] ^-alphai-Q-rdimethylamino^ethylVl-neopentyl-lH-benzordlimidazol-S-ylsulfonvDmet hyPpiperidin- l-yls)QH-pyrazol-4-yls)methanone hydrochloride. [Chem.90][0440] STEP A tert-butyl 4-((l-(2-(dimethylaminos)ethyls)-2-neopentyl-lH-benzo[dlimidazol-5-ylthios)methvls)pip eridine- 1 -carboxvlate.[Chem.91][0441] A mixture of2-(5-bromo-2-neopentyl-lH-benzo[d]imidazol-l-yl)-N,N-dimethylethanamine (prepared in STEP A of Example 1, 1.41 g, 4.15 mmol), tert-butyl 4-(mercaptomethyl)piperidine-l-carboxylate (prepared in STEP B of Example 5, 1.20 g, 5.19 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (120 mg, 0.208 mmol), tris(dibenzylideneacetone)dipalladium(0) (95.2 mg, 0.104 mmol) and N,N-diisopropylethylamine (1.09 mL, 6.23 mmol) in 1,4-dioxane (8.5 mL) was stirred at 1300C for 18 h. The mixture was filtered through a celite and the filtrate was concentrated in vacuo. The residue (2.40 g) was used for the next step without purification.[0442] MS (ESI) m/z 489 (M+H)+.

References: [1]Patent: WO2010/84767,2010,A1 .Location in patent: Page/Page column 83.

9
[ 886049-63-4 ]
[ 581060-27-7 ]
C₂₇H₄₁N₃O₂S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 236 - 240.

10
[ 895126-44-0 ]
[ 581060-27-7 ]

Yield	Reaction Conditions	Operation in experiment
5.6 g	With water; sodium hydroxide; In methanol; at 60℃; for 2h;Inert atmosphere;	A solution of tert-butyl 4-((carbamimidoylthio)methyl)piperidine-1-carboxylate (1.2, 15 g, 1.00 equiv, crude) and sodium hydroxide (2.2 g, 55.00 mmol, 1.00 equiv) in 1:2 (v/v) CH3OH/H2O (150 mL) was stirred for 2 h at 60 C. under argon. Then the reaction mixture was cooled to room temperature. The pH value of the solution was adjusted to 7 with HCl(aq) (35%). The resulting solution was extracted with EtOAc (350 mL) and the organic layers were combined. The organic layer was washed with brine (250 mL). The mixture was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (EtOAc/petroleum ether=1:8 (v/v)) to provide 5.6 g (44%) as yellow oil. 1H-NMR (400 MHz, CDCl3): delta 4.13 (m, 2H), 2.69 (m, 2H), 2.46 (m, 2H), 1.82 (m, 2H), 1.50 (s, 9H), 1.32 (m, 1H), 1.18 (m, 2H) ppm.

References: [1]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0078.

11
[ 581060-27-7 ]
tert-butyl 4-(((1-isopropyl-1H-pyrazol-4-yl)sulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]

References: [1]Patent: US2016/243100,2016,A1 .

12
[ 581060-27-7 ]
4-(((1-isopropyl-1H-pyrazol-4-yl)sulfonyl)methyl)piperidine [ No CAS ]

References: [1]Patent: US2016/243100,2016,A1 .

13
[ 581060-27-7 ]
4-(((1-isopropyl-1H-pyrazol-4-yl)sulfonyl)methyl)-N-(pyridin-4-yl)piperidine-1-carboxamide [ No CAS ]

References: [1]Patent: US2016/243100,2016,A1 .

14
[ 313735-62-5 ]
[ 581060-27-7 ]
tert-butyl 4-(((1-isopropyl-1H-pyrazol-4-yl)thio)methyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃;Inert atmosphere;	A solution of tert-butyl 4-(mercaptomethyl)piperidine-1-carboxylate (1.3, 300 mg, 1.30 mmol, 1.00 equiv), Xantphos (123 mg, 0.21 mmol, 0.20 equiv), Pd2(dba)3-CHCl3 (144 mg, 0.10 equiv), 4-bromo-1(propan-2-yl)-1H-pyrazole (246 mg, 1.30 mmol, 1.00 equiv) and N,N-diisopropylethylamine (195 mg, 1.51 mmol, 1.50 equiv) in 1,4-dioxane (5 mL) was stirred overnight at 90 C. under argon. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (EtOAc/petroleum ether=7:3 (v/v)) to provide 400 mg (crude) of a yellow oil. The product was used directly in the next step without further purification.

References: [1]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0079.

15
1,3-dimethyl-4,5-dihydro-1H-pyrazol-5-yl trifluoromethanesulfonate [ No CAS ]
[ 581060-27-7 ]
tert-butyl 4-(((1,3-dimethyl-1H-pyrazol-5-yl)thio)methyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 4h;	To a solution of 1,3-dimethyl-4,5-dihydro-1H-pyrazol-5-yl trifluoromethanesulfonate (23.2, 1.9 g, 7.78 mmol) in 1,4-dioxane (50 mL) was added <strong>[581060-27-7]tert-butyl 4-(mercaptomethyl)piperidine-1-carboxylate</strong> (1.3, 1.8 g, 7.78 mmol), potassium carbonate (2.69 g, 19.46 mmol), Xantphos (0.450 g, 0.78 mmol), and Pd2(dba)3 (0.403 g, 0.44 mmol). The resulting solution was stirred for 4 h at 100 C. The reaction mixture was cooled to room temperature, the solids were removed by filtration, and the filtrate was concentrated. The resulting residue was purified by flash chromatography (22% EtOAc in petroleum ether) to provide the desired product as a yellow oil (1.95 g, 77%). 1H NMR (300 MHz, CDCl3): delta 6.08 (s, 1H), 4.13-4.09 (m, 2H), 3.84 (s, 3H), 2.71-2.63 (m, 4H), 2.25 (s, 3H), 1.82 (d, J=12.9 Hz, 2H), 1.60-1.50 (m, 1H), 1.45 (s, 9H), 1.23-1.12 (m, 2H) ppm.

References: [1]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0225.

16
[ 166815-96-9 ]
[ 581060-27-7 ]

References: [1]Patent: US2016/243100,2016,A1 .
[2]Patent: WO2004/56773,2004,A1 .

17
[ 123855-51-6 ]
[ 581060-27-7 ]