142355-83-7|4-(1-Boc-4-piperidyl)-1-butanol| Ambeed

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Quality Control of [ 142355-83-7 ] Purity: 98% SDS Specification

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Product Details of [ 142355-83-7 ]

CAS No. :	142355-83-7
Formula :	C₁₄H₂₇NO₃
M.W :	257.37
SMILES Code :	CC(C)(C)OC(=O)N1CCC(CCCCO)CC1
MDL No. :	MFCD03265708
InChI Key :	GVOGVPFQDCQZNP-UHFFFAOYSA-N
Pubchem ID :	2784670

Safety of [ 142355-83-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 142355-83-7 ]

* 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 [ 142355-83-7 ]

[ 142355-83-7 ] Synthesis Path-Downstream 1~37

1
[ 142355-83-7 ]
[ 142355-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 1h;	Tert-butyl 4- (4-hydroxybutyl) piperidine-1-carboxylate (3 g, 11.67 mmol) was added to a round bottom flask, and the reaction product was dissolved in acetonitrile (40 mL). Then, triphenylphosphine (6 g) and carbon tetrabromide (9 g) were added. At room temperatureThe mixture was stirred for 1 hour and extracted several times with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over sodium sulfate, and then concentrated. The obtained filtrate was purified by chromatography to obtain the desired compound as a colorless liquid.

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2537 - 2551.
[2]Organic Letters,2002,vol. 4,p. 549 - 552.
[3]Patent: KR101663543,2016,B1 .Location in patent: Paragraph 0105-0108.

2
[ 142247-38-9 ]
[ 142355-83-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step B 4-(1-t-Butoxycarbonylpiperidin-4-yl)butan-1-ol The title compound was prepared from 400 mg (1.5 mmol) of 4-(1-t-butoxycarbonylpiperidin-4-yl)butanoic acid (from EXAMPLE 103, Step A) using a procedure analogous to that described in EXAMPLE 30, Step D. 200 mg (53%) of the title compound was obtained: 1H NMR (500 MHz) δ 1.16 (dq, J=3.9, 8.3, 2H). 1.26-1.29 (2H), 1.47-1.42 (3H), 1.46 (s, 10H), 1.55-1.58 (2H), 1.65 (bd, 2H), 2.67 (bt, 2H), 3.65 (t, J=6.6, 1H). 4.07 (bd, 2H).
	With borane-THF; In tetrahydrofuran; at 20 - 80℃; for 3h;Sealed tube; Inert atmosphere;	Fatty acid 3ab (0.796g, 2.95 mmol,Prepared in Example 11) and the magnet, sealed with a rubber stopper and then protected by nitrogen,Take 4.5 mL of 1mol/L borane tetrahydrofuran solution (4.5 mol) and slowly drop it into the flask,After the dripping, the reaction was carried out at room temperature for 1 hour, and then transferred to an oil bath at 80C for 2 hours. After the reaction is completed, it is cooled to room temperature, and anhydrous methanol is slowly added dropwise to quench the remaining borane.Direct vacuum distillation to remove the solvent, column chromatography (petroleum ether: ethyl acetate = 3:1) to separate the primary alcohol product 4ad (0.622g, 2.42 mmol).The hydrogen nuclear magnetic spectrum and carbon spectrum of the primary alcohol product 4ad are shown in Figures 23-24.

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 2537 - 2551.
[2]Patent: US6265434,2001,B1 .
[3]Patent: CN111718228,2020,A .Location in patent: Paragraph 0092-0093.

3
[ 142355-83-7 ]
[ 146873-76-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step C 4-(1-t-Butoxycarbonylpiperidin-4-yl)butanal The title compound was prepared from 200 mg (0.79 mmol) of 4-(1-t-butoxycarbonylpiperidin-4-yl)butan-1-ol (from EXAMPLE 103, Step B) using a procedure analogous to that described in EXAMPLE 1, Step I. 153 mg (77%) of the title compound was obtained: 1H NMR (500 MHz) δ 1.10 (dq, J=4.4, 8.2, 2H). 1.25-1.30 (2H), 1.38-1.44 (m, 1H), 1.46 (s, 9H), 1.63-1.69 (4H), 2.44 (dt, J=1.7, 5.7, 2H). 2.67 (bt, 2H), 4.8 (bs, 2H), 9.77 (t, J=1.8, 1H).
	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 1h;	Preparation 11: 4-(4-Oxobutyl)piperidine-l-carboxylic acid tert-butyl esterA stirred suspension of Dess-Martin periodinane (165 mg, 391 μmol) in CH2Cl2 (3 mL) was cooled on ice and a solution of 4-(4-hydroxybutyl)piperidine-l-carboxylic acid tert-butyl ester in CH2Cl2 (2 mL) added. Stirring was continued for 1 h at rt whereupon the solvent was evaporated and the residue taken up in ether (20 mL). The organic phase was washed with brine (3 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography (IH-Et2O 2:1) to afford the title aldehyde: δH (CDCl3) 1.09 (dq, 2H), 1.25-1.30 (m, 2H), 1.36- 1.45 (m, IH), 1.46 (s, 9H), 1.62-1.70 (m, 4H), 2.44 (t, 2H), 2.68 (t, 2H), 4.08 (m, 2H), 9.78 (s, IH).
	With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 3h;	To a mixture of tert-butyl 4-( 4-hydroxybutyl)piperidine-1-carboxylate (2 g, 7.8 mmol) inDCM (40 mL) cooled to 0 oc was added pyridinium chlorochromate (2.5 g, 11.7 mmol). The mixture was stirred at room temperature for 3 h. Then the mixture was poured into ether(500 mL) and filtered. The filtrate was washed with water until the aqueous phase was colorless.The organic phase was dried and concentated to give tert-butyl 4-( 4-oxobutyl )piperidine-1-carboxylate. LRMS m/z (M+Na) 278.1 found, 278.2 required.

1.427 g

To a solution of oxalyl chloride (757.49 mg, 5.968 mmol, 1.2 equiv) in DCM (7.5 ml_) was added DMSO (408.01 mg, 5.222 mmol, 1 .05 equiv) in DCM (8.00 ml_) dropwise at -78 C under nitrogen atmosphere. The resulting mixture was stirred for 5 min at -78 C followed by addition of tert-butyl 4-(4- hydroxybutyl)piperidine-1-carboxylate (1.28 g, 4.973 mmol, 1.00 equiv) in DCM (6.5 ml_). The resulting mixture was stirred for additional 15 min at -78 C, followed by the addition of TEA (2.52 g, 24.867 mmol, 5 equiv) at -78 C. The resulting mixture was stirred for additional 10 min at -78 C, warmed to room temperature, and stirred for an additional 2 hours. The mixture was extracted with CH2CI2 (3 x 20 ml_). The combined organic layers were washed with brine (3 x 30 ml_), dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure. This provided Intermediate 2 (1 .427 g) as a light yellow oil; LCMS (ESI) m/z: [M+H]+ = 256.

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 50 - 60.
[2]Patent: US6265434,2001,B1 .
[3]Patent: WO2007/3962,2007,A2 .Location in patent: Page/Page column 21.
[4]Patent: WO2018/68296,2018,A1 .Location in patent: Page/Page column 36; 37.
[5]Patent: WO2018/68295,2018,A1 .Location in patent: Page/Page column 108.
[6]Patent: WO2021/155321,2021,A2 .Location in patent: Page/Page column 321.

4
[ 403857-14-7 ]
[ 142355-83-7 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

5
[ 7037-49-2 ]
[ 142355-83-7 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

6
[ 2629-72-3 ]
[ 142355-83-7 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

7
[ 156185-63-6 ]
[ 142355-83-7 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

8
[ 142355-83-7 ]
[ 142356-28-3 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2537 - 2551.

9
[ 142355-83-7 ]
[ 142373-59-9 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2537 - 2551.

10
[ 142355-83-7 ]
[ 142355-84-8 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.
[2]Journal of Medicinal Chemistry,1994,vol. 37,p. 2537 - 2551.

11
[ 142355-83-7 ]
C₃₅H₅₀N₂O₈S [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

12
[ 142355-83-7 ]
[ 403857-10-3 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

13
[ 142355-83-7 ]
4-[4-(4-{2-(butane-1-sulfonylamino)-2-[2-(1,1-dimethyl-3-oxo-propyl)-3,5-dimethoxy-phenoxycarbonyl]-ethyl}-phenoxy)-butyl]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

14
[ 142355-83-7 ]
4-[4-(4-{2-(butane-1-sulfonylamino)-2-[2-(3-hydroxy-1,1-dimethyl-propyl)-3,5-dimethoxy-phenoxycarbonyl]-ethyl}-phenoxy)-butyl]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

15
[ 142355-83-7 ]
[ 403857-09-0 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

16
[ 142355-83-7 ]
[ 403857-08-9 ]

References: [1]Organic Letters,2002,vol. 4,p. 549 - 552.

17
[ 165528-85-8 ]
[ 142355-83-7 ]