1240390-32-2|(3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol| Ambeed

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Quality Control of [ 1240390-32-2 ] Purity: 98% SDS Specification

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Product Details of [ 1240390-32-2 ]

CAS No. :	1240390-32-2
Formula :	C₅H₁₁NO₂
M.W :	117.15
SMILES Code :	O[C@@H]1[C@@H](N)COCC1
MDL No. :	MFCD19215826
InChI Key :	KUCSFTQJADYIQH-WHFBIAKZSA-N
Pubchem ID :	55285677

Safety of [ 1240390-32-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1240390-32-2 ]

* 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 [ 1240390-32-2 ]
Downstream synthetic route of [ 1240390-32-2 ]

[ 1240390-32-2 ] Synthesis Path-Upstream 1~1

1
[ 1240390-32-2 ]
[ 1240390-36-6 ]

References: [1] Patent: WO2013/78468, 2013, A1, .
[2] Patent: US2017/15655, 2017, A1, .

[ 1240390-32-2 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 1240390-32-2 ]
[ 1240390-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol; at 20℃; for 21.5h;Product distribution / selectivity;	,5-anhydro-2,4-dideoxy-2-([(1,1-dimethylethyl)oxy]carbonyl}amino)-L-threo- pentitolMethod 12-amino-1 ,5-anhydro-2,4-dideoxy-L-threo-pentitol (~184g) in methanol (1300ml) was treated with triethylamine (22ml). Bis(1 ,1-dimethylethyl) dicarbonate (369g) was dissolved in methanol (530ml) was added to the mixture over 35min and washed in with methanol (30ml). The reaction was stirred at 200C for -21.5h and concentrated under reduced pressure. TBME (280ml) and cyclohexane (2520ml) were added to the residue and the mixture rotated at 200C for ~2.5h. The resulting solid was isolated by filtration and washed with cyclohexane (2x 780ml). The solid was dried at 30-35C under vacuum to give the title compound as a white solid (325.76g).1 H NMR (400MHz, D6-DMSO): δH 6.60(1 H, bd), 4.77(1 H, d), 3.72(2H, m), 3.39(1 H, m), 3.26-3.1 1 (2H, m), 2.89(1 H, t), 1.82(1 H, m), 1.38(1 OH, m).
970 mg	With triethylamine; In methanol; at 20℃; for 15h;	Step 5: To a solution of<strong>[1240390-32-2](3S,4S)-3-aminotetrahydro-2H-pyran-4-ol</strong> (600 mg, 5.13mmol) in MeOH (4 ml) was added Et3N (0.1 ml) and a solution of Boc2O (1.2 g, 5.5 mmol) inMeOH (2 ml). After stirred at room temperature for 15 h, it was concentrated and added MTBE(1 ml) and Hexanes (9 ml), the resulting solid was then collected by filtration to give tert-butyl(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-ylcarbamate (970 mg).
200 g	With triethylamine; In methanol; at 10 - 35℃;	To a mixture of <strong>[1240390-32-2]2-amino-1,5-anhydro-2,4-dideoxy-L-threo-pentitol</strong> (120 g), methanol (1200 mL) and TEA (124 g) was added a mixture of di-tert-butyl dicarbonate (240 g) and methanol (530 mL) over 35 min or longer, the container used for addition was washed with methanol (30 ml), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and dichloromethane (1000 ml) was added thereto. The mixture was washed with 1 M hydrochloric acid (500 ml) and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (200 g). (1469) 1HNMR (400 MHz, DMSO-d6): δ 1.34-1.38 (10H, m), 1.80-1.84 (1H, m), 2.86-2.91 (1H, m), 3.15-3.26 (2H, m), 3.35-3.41 (1H, m), 3.67-3.77 (2H, m), 4.80 (1H, s), 6.64 (1H, d, J=8.0 Hz).

References: [1]Patent: WO2010/97248,2010,A1 .Location in patent: Page/Page column 37.
[2]Patent: WO2013/78468,2013,A1 .Location in patent: Paragraph 0752.
[3]Patent: US2017/15655,2017,A1 .Location in patent: Paragraph 1468-1469.

2
[ 1240390-30-0 ]
[ 1240390-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Pearlman's catalist; In ethanol; water; at 25℃; under 775.743 Torr;Inert atmosphere;Product distribution / selectivity;	2-amino-1,5-anhydro-2,4-dideoxy-L-threo-pentitol Method 1A mixture of 1 ,5-anhydro-2,4-dideoxy-2-[(1 S)-1-phenylethyl]amino}-L-threo-pentitol (348.6g) and palladium hydroxide on charcoal (20% w/w, wet with ca. 50% water, 35g) were suspended in ethanol (5230ml). The reaction vessel was charged with hydrogen (15psi) and vented (x2), and then the mixture hydrogenated under 15psi of hydrogen at ca 25C overnight. The vessel was purged with nitrogen (x8), then with hydrogen (x1 ) and hydrogenation under 15psi of hydrogen continued for ~5h. The vessel was purged with nitrogen (x5), then hydrogen (x1 ) and hydrogenation under 15psi of hydrogen continued for ~15h. The reaction was filtered through Celite and then through a 1 micron Dominick Hunter before evaporation of the solvent in vacuo. The residue was dissolved in methanol with warming, filtered through Celite, then through a 0.2 micron Dominick Hunter before evaporation of the solvent in vacuo to leave the title compound. This material was used without further purification.1 H NMR (400MHz, D6-DMSO includes): δH 3.76(1 H, d), 3.69(1 H, dd), 3.26(1 H, t), 3.14(1 H, m), 2.85(1 H, t), 2.39(1 H, m), 1.74(1 H, dd), 1.36(1 H, m).
600 mg	With 10 wt% Pd(OH)2 on carbon; hydrogen; In ethanol; under 1551.49 Torr; for 15h;	Step 4: To a solution of (3S,4S)-3 -((S)-1-phenylethylamino)tetrahydro-2H-pyran-4-ol (1.47 g, 6.65 mmol) in EtOH (25 ml) was added Pd(OH)2/C (200 mg), charged with H2 (30 psi) in a parr shaker, and was shaked for 15 h, Pd(OH)2/C was filtered off, the filtrate was concentrated to give (3S, 4S)-3-aminotetrahydro-2H-pyran-4-ol (600 mg).

References: [1]Patent: WO2010/97248,2010,A1 .Location in patent: Page/Page column 36.
[2]Patent: WO2013/78468,2013,A1 .Location in patent: Paragraph 0751.

3
[ 1240390-31-1 ]
[ 1240390-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Pearlman's catalist; In methanol; at 50℃; under 37503.8 Torr;Inert atmosphere; H-cube;	Method 31 ,5-Anhydro-2,4-dideoxy-2-[(1 R)-1-phenylethyl]amino}-L-threo-pentitol (80mg) was dissolved in methanol (8ml). The reaction was hydrogenated using H-cube flow hydrogenation (settings: 500C, 50 bar, 1 ml/min flow rate) over Palladium hydroxide on Carbon (20%,CatCart 30). The resulting solution was reduced to dryness under a stream of nitrogen and the resulting white solid dried in vacuo to give 2-amino-1 ,5- anhydro-2,4-dideoxy-L-threo-pentitol (21 mg).1 H NMR (400MHz, D6-DMSO includes): δH 3.76(1 H, m), 3.69(1 H, m), 3.26(1 H, m), 3.15(1 H, m), 2.85(1 H, m), 2.40(1 H, m), 1.74(1 H, m), 1.35(1 H, m). Rotation: +31 , c=1.016 in methanol at 25.2C.

References: [1]Patent: WO2010/97248,2010,A1 .Location in patent: Page/Page column 36.

4
[ 29943-42-8 ]
[ 1240390-32-2 ]

References: [1]Patent: WO2012/158475,2012,A1 .
[2]Patent: WO2011/75371,2011,A1 .
[3]Patent: WO2011/84368,2011,A1 .
[4]Patent: WO2011/25851,2011,A1 .

5
[ 104681-92-7 ]
[ 1240390-32-2 ]

References: [1]Patent: WO2012/158475,2012,A1 .
[2]Patent: WO2011/75371,2011,A1 .
[3]Patent: WO2011/84368,2011,A1 .
[4]Patent: WO2011/25851,2011,A1 .

6
[ 693245-80-6 ]
[ 1240390-32-2 ]

References: [1]Patent: WO2012/158475,2012,A1 .
[2]Patent: WO2011/84368,2011,A1 .
[3]Patent: WO2011/25851,2011,A1 .

7
[ 1268516-31-9 ]
[ 1240390-32-2 ]

References: [1]Patent: WO2012/158475,2012,A1 .
[2]Patent: WO2011/75371,2011,A1 .
[3]Patent: WO2011/84368,2011,A1 .
[4]Patent: WO2011/25851,2011,A1 .

8
[ 1268516-32-0 ]
[ 1240390-32-2 ]

References: [1]Patent: WO2012/158475,2012,A1 .
[2]Patent: WO2011/75371,2011,A1 .
[3]Patent: WO2011/84368,2011,A1 .
[4]Patent: WO2011/25851,2011,A1 .

9
[ 1268516-33-1 ]
[ 1240390-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;10 wt% Pd(OH)2 on carbon; In methanol; at 25℃; under 2068.65 Torr; for 15h;	To a solution of the above compound (90.5 g, 0.360 mol) in 1.8 L of methanol was added palladium hydroxide on carbon (9 g). The mixture was subjected to 40 psi of hydrogen at 25 C for 15 h, then filtered through solka-floc. The filter cake was washed 3x with methanol (200 mL), and the combined filtrates were concentrated in vacuo to provide crude (3S, 4S)-3- aminotetrahydro-2H-pyran-4-ol that gave proton NMR spectra consistent with theory.
	With hydrogen;10 wt% Pd(OH)2 on carbon; In methanol; at 25℃; under 2068.65 Torr; for 15h;	To a solution of the above compound (90.5 g, 0.360 mol) in 1.8 L of methanol was added palladium hydroxide on carbon (9 g). The mixture was subjected to 40 psi of hydrogen at 25 C for 15 h, then filtered through solka-floc. The filter cake was washed 3x with methanol (200 mL), and the combined filtrates were concentrated in vacuo to provide crude (35, 4S)~3- aminotetrahydro-2H-pyran-4-ol that gave proton NMR spectra consistent with theory.
	With hydrogen;10 wt% Pd(OH)2 on carbon; In methanol; at 25℃; under 2068.65 Torr; for 15h;	To a solution of the above compound (90.5 g, 0.360 mol) in 1.8 L of methanol was added palladium hydroxide on carbon (9 g). The mixture was subjected to 40 psi of hydrogen at 25 C for 15 h, then filtered through solka-fioc. The filter cake was washed 3x with methanol (200 mL), and the combined filtrates were concentrated in vacuo to provide crude (3S, 4S)-3- aminotetrahydro-2H-pyran-4-ol that gave proton NMR spectra consistent with theory.

With hydrogen;10 wt% Pd(OH)2 on carbon; In methanol; at 25℃; under 2068.65 Torr; for 15h;

To a solution of the above compound (90.5 g, 0.360 mol) in 1.8 L of methanol was added palladium hydroxide on carbon (9 g). The mixture was subjected to 40 ps of hydrogen at 25 0C for 15 h, then filtered through solka-floc. The filter cake was washed 3x with methanol (200 mL), and the combined filtrates were concentrated in vacuo to provide crude (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol that gave proton NMR spectra consistent with theory.

References: [1]Patent: WO2012/158475,2012,A1 .Location in patent: Page/Page column 56.
[2]Patent: WO2011/75371,2011,A1 .Location in patent: Page/Page column 52; 53.
[3]Patent: WO2011/84368,2011,A1 .Location in patent: Page/Page column 51.
[4]Patent: WO2011/25851,2011,A1 .Location in patent: Page/Page column 84.

10
[ 209003-46-3 ]
[ 1240390-32-2 ]
[ 1314141-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 16h;	4-Bromoquinoline-2-carboxylic acid (A3) was prepared as described in Example 1.To a solution of A3 (0.35 g, 1.4 mmol) in 6.0 mL CH2C12 was added (3S,4S)-3-aminotetrahydro- 2H-pyran-4-ol (0.20 g, 1.7 mmol). BOP reagent (0.74 g, 1.7 mmol), and triethylamine (0.58 mL, 4.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2CI2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 25-100% ethyl acetate in hexanes to afford 4-bromo-N-[(35,4S,)-4-hydroxytetrahydro-2H-pyran-3-yl]quinoline-2-carboxamide that gave a mass ion (ES+) of 353.1 (81Br) for M+H+.

References: [1]Patent: WO2011/84368,2011,A1 .Location in patent: Page/Page column 51.

11
[ 25637-16-5 ]
[ 1240390-32-2 ]