1165923-86-3|5-Methyl-1,2,3,4-tetrahydroisoquinolin-6-ol| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1165923-86-3 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1165923-86-3 ]

CAS No. :	1165923-86-3
Formula :	C₁₀H₁₃NO
M.W :	163.22
SMILES Code :	OC1=C(C)C2=C(CNCC2)C=C1
MDL No. :	N/A

Safety of [ 1165923-86-3 ]

Application In Synthesis of [ 1165923-86-3 ]

* 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 [ 1165923-86-3 ]

[ 1165923-86-3 ] Synthesis Path-Downstream 1~11

1
[ 24424-99-5 ]
[ 1165923-86-3 ]
[ 1165923-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃;	Preparation 14: 1,1-Dimethylethyl 6-hydroxy-5-methyl-3,4-dihydro-2(1H)- isoquinolinecarboxylate. To a suspension of 5-methyl-1 ,2,3,4-tetrahydro-6-isoquinolinol (Preparation 13;_163 mg; I .Ommol) in dichloromethane (5ml) at O0C was added triethylamine (0.21 ml; 1.50 mmol) followed by bis(1,1-dimethylethyl) dicarbonate (240 mg; 1.10mmol ). The solvent was evaporated and the residue partitioned between ethyl acetate and brine. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were dried (MgSO4) and evaporated to give a yellow oil. Purification by flash chromatography eluting with a gradient of 5-25% ethyl acetate in cyclohexane gave the title compound as a white foam (232mg). MS m/z 262 [M-H].
295 mg	With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 0.0833333h;	To a solution of 5-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol (355mg) in 1 N aq. NaOH (3.6ml) was added di-tert-butyldicarbonate (850mg) in dioxane (20ml). The reaction mixture was stirred at rt for 5min. The mixture was diluted with DCM (20ml)and 1 N aq. HCI (5ml). The aq. layer was extracted with DCM and the combined org. layers were washed with sat. aq. NaCI., dried over MgS04, filtrated off and evaporated in vacuo. The crude was purified by CC (Buchi Sepacore, 10g cartridge, solvent A: DCM, solvent B: MeOH, gradient in %B: 0 to 5, flow rate: 6ml/min) to afford 295mg of a yellow oil. LC-MS (A): tR = 0.84min; [M+H]+: 264.12.

References: [1]Patent: WO2009/80724,2009,A1 .Location in patent: Page/Page column 27-28.
[2]Patent: WO2016/177690,2016,A1 .Location in patent: Page/Page column 89.

2
[ 1165923-84-1 ]
[ 1165923-86-3 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 13: 5-Methyl-1,2,3,4-tetrahydro-6-isoquinolinol. To a solution of 5-methyl-6-(methyloxy)-3,4-dihydro-2(1 H)-isoquinolinecarbaldehyde (Preparation 12; 1.49 g; 7.26 mmol) in dichloromethane (25ml) at O0C under nitrogen was slowly added boron tribromide (9.09g; 36.3mmol). After 85min at O0C, methanol (25 ml) was added slowly, and the resulting mixture was left standing at room temperature for three days. Removal of the solvent and trituration with methanol/ dichloromethane gave a white solid residue; the mother liquors were concentrated and the residue applied to an SCX solid phase extraction cartridge (2Og) and eluted with methanol followed by 2N ammonia in methanol to elute the product. After evaporation of the solvent the title compound (780mg) was obtained as a pale yellow solid. 1H NMR (DMSOd6) δ: 8.91 (br. s., 1 H), 6.62 (d, 1 H), 6.56 (d, 1 H), 3.70 (s, 2H), 2.92 (t, 2H), 2.48 (t, 2H), 1.96 (s, 3H).
370 mg	With boron tribromide; In dichloromethane; at 0℃; for 1.41667h;	To a solution of 6-methoxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carbaldehyde (530mg) in DCM (15ml) cooled down to 0C was added borontribromide 1 M in DCM (12.2ml). The reaction mixture was stirred at 0C for 1 h25min. MeOH (10ml) was slowly added and the mixture was stirred at rt over 9 days. The solution was evaporated in vacuo and the residue was purified by CC (Buchi Sepacore, 20g cartridge, solvent A: DCM, solvent B: NH3 7N in MeOH, gradient in %B: 1 to 10, flow rate: 20ml/min) to afford 370mg of a white solid. LC-MS (A): tR = 0.36min; [M+H]+: 164.07.

References: [1]Patent: WO2009/80724,2009,A1 .Location in patent: Page/Page column 27.
[2]Patent: WO2016/177690,2016,A1 .Location in patent: Page/Page column 89.

3
N-Boc-4-piperidone [ No CAS ]
[ 1165923-86-3 ]

References: [1]Organic Process Research and Development,2013,vol. 17,p. 1239 - 1246.

4
[ 1165923-89-6 ]
[ 1165923-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 20℃; for 2h;	Intermediate 2-12 -A. 5-Methyl-1 ,2,3,4-tetrahydroisoquinolin-6-olA mixture of fe/ -butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1 /-/)-carboxylate, prepared as described in J. Med. Chem. , 2011 , 54 (19), pp 6724-6733, (2.6 g, 9.87 mmol) and TFA (7.6 mL) in CH2CI2 (20 mL) was stirred at room temperature for 2 h, and then diluted with CH2CI2 and H20. The mixture was rendered basic (pH = ~8) by addition of aq. NH4OH. The organic layer was separated, and then concentrated to furnish the title compound directly. MS (ESI+) m/z 164.0 (M+H)

References: [1]Patent: WO2016/1876,2016,A1 .Location in patent: Page/Page column 53.

5
[ 1165923-86-3 ]
[ 31106-82-8 ]
5-methyl-2-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydroisoquinolin-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	Intermediate 2-12. 5-Methyl-2-(pyridin-2-ylmethyl)-1 ,2,3,4-tetrahydroisoquinolin-6- olTo a solution of Intermediate 2-12-A (420 mg, 2.57 mmol) in CH2CI2 (12 mL) and triethylamine (1 .18 mL, 8.49 mmol) at 0 C was added 2-(bromomethyl)pyridine hydrobromide (781 mg, 3.09 mmol). The mixture was stirred at room temperature for 16 h, and then diluted with CH2CI2 and H20. The organic layer was separated. The aqueous layer was then extracted with CH2CI2. The organic layers were then combined and concentrated. The resulting residue was purified by silica gel flash column chromatography (heptane/EtOAc = 1 /0 to 0/1) to afford the title compound. MS (ESI+) m/z 255.2 (M+H).

References: [1]Patent: WO2016/1876,2016,A1 .Location in patent: Page/Page column 53.

6
[ 56724-03-9 ]
[ 1165923-86-3 ]