233764-32-4|4-Amino-1-methylcyclohexanol| Ambeed

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Quality Control of [ 233764-32-4 ] Purity: 98% SDS Specification

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Product Details of [ 233764-32-4 ]

CAS No. :	233764-32-4
Formula :	C₇H₁₅NO
M.W :	129.20
SMILES Code :	OC1(C)CCC(N)CC1
MDL No. :	MFCD14706208
InChI Key :	KUKASNZJTIKRMH-UHFFFAOYSA-N
Pubchem ID :	18331273

Safety of [ 233764-32-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 233764-32-4 ]

* 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 [ 233764-32-4 ]

[ 233764-32-4 ] Synthesis Path-Downstream 1~32

1
[ 179321-49-4 ]
[ 233764-32-4 ]

References: [1]Patent: WO2011/6074,2011,A1 .
[2]Patent: WO2013/96744,2013,A1 .
[3]Patent: EP3072893,2016,A1 .

2
tert-butyl N-(4-hydroxy-4-methylcyclohexyl)carbamate [ No CAS ]
[ 233764-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20℃; for 1h;	Step B: Preparation of 5-((RV2-(2.5-difluorophenyl>pyrrolidin- 1 -vO-N-(4- hydroxy-4-rnethylcyclohexyDpyrazolo [ 1 ,5 -a"\|pyrimidine-3 -carboxamide (Diasteromer 1 ).; The minor isomer from Step A (45.1 mg, 0.197 mmol) was dissolved in DCM (1.0 mL) and 4N HCl in dioxane (492 μL, 1.97 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour and was concentrated to afford 4-amino-l-methylcyclohexanol (minor isomer). The 4-amino-l-methylcyclohexanol was reacted with (R)-5-(2-(2,5- difluorophenyl)pyrrolidin-l-yl)pyrazolo[l,5-a]pyrimidine-3-carboxylic acid (Preparation C) according to the procedure outlined in Example 1 to provide the title product as a white solid (14 mg, 48% yield). MS (apci) m/z = 456.1 (M+H).
1.3 g	With trifluoroacetic acid; In tetrahydrofuran; at 20℃;	To a solution of Compound 2 (970 mg, 4.43 mmol) in DCM (10 mL) was added TFA (5 mL). The formed mixture was stirred overnight at rt. The reaction mixture was concentrated to give the product A121 (1.3 g,), which was used in the next step directly.
0.5 g	With hydrogenchloride; In methanol; at 20℃; for 7h;	Intermediate 459: 4-amino-1-methylcyclohexanol 0.6 g of Intermediate 458 was dissolved in 70 ml of HCl/MeOH (10%), and stirred at room temperature for 7 h. The reaction solution was evaporated to dryness, and dried along with 3 * 20 ml of dichloromethane to afford a dark brown solid (0.5 g).

References: [1]Patent: WO2011/6074,2011,A1 .Location in patent: Page/Page column 104.
[2]Patent: WO2013/96744,2013,A1 .Location in patent: Page/Page column 216.
[3]Patent: EP3072893,2016,A1 .Location in patent: Paragraph 0457; 0458.

3
[ 4746-97-8 ]
[ 233764-32-4 ]

References: [1]Patent: WO2011/139107,2011,A2 .
[2]Patent: WO2014/9302,2014,A1 .
[3]Patent: US2015/158879,2015,A1 .
[4]Patent: US2016/200741,2016,A1 .

4
[ 66336-42-3 ]
[ 233764-32-4 ]

References: [1]Patent: WO2011/139107,2011,A2 .
[2]Patent: WO2014/9302,2014,A1 .
[3]Patent: US2015/158879,2015,A1 .

5
[ 952745-69-6 ]
[ 233764-32-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 5% Pd/C; hydrogen; In methanol; at 20℃;	Step 4: synthesis of 4-amino-i -methylcyclohexanol A solution of 4-(benzylamino)-i-methylcyclohexanol (4.9 g, 22.3 mmol) in MeOH (150 mL) was stilTed with 7% Pd/C (700 mg) under H2 atmosphere at RT overnight. The resulting mixture was filtered to remove Pd/C and the filtrate was concentrated in vacuo to afford a white solid (2.9 g, quantitive yield) which was used in the next step directly.
100%	With 5% Pd/C; hydrogen; In methanol; at 20℃;	Step 4: synthesis of 4-amino-1-methylcyclohexanol A solution of 4-(benzylamino)-1-methylcyclohexanol (4.9 g, 22.3 mmol) in MeOH (150 mL) was stirred with 7% Pd/C (700 mg) under H2 atmosphere at RT overnight. The resulting mixture was filtered to remove Pd/C and the filtrate was concentrated in vacuo to afford a white solid (2.9 g, quantitative yield) which was used in the next step directly.
100%	With 5% Pd/C; hydrogen; In methanol; at 20℃;	A solution of 4-(benzylamino)-1-methylcyclohexanol (4.9 g, 22.3 mmol) in MeOH (150 mL) was stirred with 7% Pd/C (700 mg) under H2 atmosphere at RT overnight. The resulting mixture was filtered to remove Pd/C and the filtrate was concentrated in vacuo to afford a white solid (2.9 g, quantitative yield) which was used in the next step directly.

83%

With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 31h;

Step 2: Synthesis of 4-amino-1-methylcyclohexanol [628] 4-(Benzylamino)-1-methylcyclohexanol (335 mg, 1.53 mmol) was dissolved in EtOH (7.95 ml), followed by addition of Pd (10 wt% on activated carbon, 35 mg), and then the resulting liquid was stirred at room temperature under hydrogen stream for 31 hours. The resulting reaction liquid was filtered, concentrated under reduced pressure, and dried under vacuum, to obtain 164 mg of white solid (83 %).[629]

References: [1]Patent: WO2014/9302,2014,A1 .Location in patent: Page/Page column 90; 91.
[2]Patent: US2015/158879,2015,A1 .Location in patent: Paragraph 0443; 0444.
[3]Patent: US2016/200741,2016,A1 .Location in patent: Paragraph 0444-0445.
[4]Patent: WO2011/139107,2011,A2 .Location in patent: Page/Page column 108-109.

6
[ 233764-32-4 ]
[ 87951-12-0 ]
ethyl 1-(4-hydroxy-4-methylcyclohexyl)-1H-imidazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
462 mg	at 75℃; for 8h;	This crude product and ethyl 3-(dimethylamino)-2-isocyanoacrylate (450 mg) were mixed and stirred at 75C for 8 hours. To the reaction solution, saturated aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-ethyl acetate) to obtain a diastereomeric mixture of the title compound (462 mg, trans:cis=1:3). 1H-NMR (CDCl3) δ: 1.31 (2.25H, s), 1.34 (0.75H, s), 1.38 (3H, t, J = 7.0 Hz), 1.52-1.70 (2H, m), 1.77-1.96 (4H, m), 2.08-2.19 (2H, m), 3.93 (0.75H, tt, J = 12.2, 3.9 Hz), 4.06 (0.25H, m), 4.12 (0.5H, q, J = 7.0 Hz), 4.36 (1.5H, q, J = 7.0Hz), 7.57 (1H, s), 7.68 (0.25H, s), 7.70 (0.75H, s).

References: [1]Patent: EP2548871,2013,A1 .Location in patent: Paragraph 0244-0246.

7
benzyl (4-hydroxy-4-methylcyclohexyl)carbamate [ No CAS ]
[ 233764-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; water; hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 15h;	[Step 2] Ethyl 1-(4-hydroxy-4-methylcyclohexyl)-1H-imidazole-4-carboxylate The compound obtained in Step 1 of this Reference Example was dissolved in ethanol (12 mL). To the solution, 10% palladium-carbon catalyst (hydrated, 400 mg) was added, and the mixture was stirred at room temperature for 15 hours under a hydrogen atmosphere at normal pressure. After filtration through celite, the filtrate was concentrated under reduced pressure to obtain a crude product of 4-amino-1-methylcyclohexanol.

References: [1]Patent: EP2548871,2013,A1 .Location in patent: Paragraph 0244-0246.

8
[ 233764-32-4 ]
5-amino-2-[1-(4-hydroxy-4-methylcyclohexyl)-1H-imidazol-4-yl]methyl}valeric acid [ No CAS ]