Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 218595-25-6 Chemical Structure| 218595-25-6

Structure of 218595-25-6

Chemical Structure| 218595-25-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

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

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 218595-25-6 ]

CAS No. :218595-25-6
Formula : C6H13NO2
M.W : 131.17
SMILES Code : COC[C@@H]1NCCOC1
English Name :(S)-3-(Methoxymethyl)morpholine
MDL No. :MFCD14586376
InChI Key :ROHMLTGBCWLCIW-RGMNGODLSA-N
Pubchem ID :53338714

Safety of [ 218595-25-6 ]

Application In Synthesis of [ 218595-25-6 ]

* 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 [ 218595-25-6 ]

[ 218595-25-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 75-15-0 ]
  • [ 218595-25-6 ]
  • [ 2089642-99-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: carbon disulfide; (3S)-3-(methoxymethyl)morpholine With potassium hydroxide In water at 50℃; Stage #2: With sodium nitrite In methanol; water at 0℃; for 0.5h;
  • 2
  • [ 101376-25-4 ]
  • [ 218595-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / 20 °C 2: sodium iodide / methanol / Reflux 3: 10% Pd/C; hydrogen / methanol / 20 °C / 760.05 Torr
  • 3
  • [ 1217697-39-6 ]
  • [ 218595-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium iodide / methanol / Reflux 2: 10% Pd/C; hydrogen / methanol / 20 °C / 760.05 Torr
  • 4
  • [ 218594-75-3 ]
  • [ 218595-25-6 ]
YieldReaction ConditionsOperation in experiment
With 10% Pd/C; hydrogen In methanol at 20℃;
  • 5
  • [ 218595-25-6 ]
  • [ 218592-73-5 ]
  • [ 218785-45-6 ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; N-ethyl-N,N-diisopropylamine; paraformaldehyde In 1,4-dioxane; methanol; chloroform; ethyl acetate 69 EXAMPLE 69 EXAMPLE 69 Paraformaldehyde (0.034 g) and copper(I) iodide (12 mg) were added to a mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(3,4-dimethylbenzyl) -4-(2-propynyl)piperazine (0.21 g), (3S)-3-methoxymethylmorpholine (0.09 g) and N,N-diisopropylethylamine (0.1 ml) in 1,4-dioxane (5 ml) and the whole was stirred at room temperature for 30 minutes and then heated at 70° C. for 2.5 hours. After cooling, ethyl acetate and sodium hydrogen carbonate solution were added to the mixture. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with 3% of methanol in chloroform as an eluent to give (2R)-1-[3,5-bis-(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[4-((3S)-3-methoxymethylmorpholino)-2-butynyl]piperazine.
  • 6
  • [ 218595-25-6 ]
  • [ 219817-43-3 ]
  • [ 2922566-51-4 ]
YieldReaction ConditionsOperation in experiment
36.8 % With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; Inert atmosphere; 30.1 Step 1 Synthesis of (S)-4-(3-chloro-5-nitrophenyl)-3-(methoxymethyl)morpholine To a mixture of (3S)-3-(methoxymethyl)morpholine (1 g, 7.60 mmol), 1-bromo-3-chloro- 5-nitrobenzene (2.16 g, 9.10 mmol), BINAP (0.95 g, 1.50 mmol) and Cs2CO3 (4.95 g, 15.20 mmol) in dioxane (10 mL) was added Pd(OAc)2 (0.34 g, 1.50 mmol), the mixture was stirred at 100 °C under N2 atmosphere for 16 hours. LC-MS was checked, and the reaction was completed. After the reaction, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether = 4% ~ 5%) to afford (S)-4-(3-chloro-5-nitrophenyl)-3-(methoxymethyl)morpholine (0.83 g, 36.8% yield) as a yellow solid. LCMS (ESI) calcd C12H16ClN2O4+[M + H]+m/z 287.08, found 286.9.
36.8 % With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; Inert atmosphere; 30.1 Step 1 Synthesis of (S)-4-(3-chloro-5-nitrophenyl)-3-(methoxymethyl)morpholine To a mixture of (3S)-3-(methoxymethyl)morpholine (1 g, 7.60 mmol), 1-bromo-3-chloro- 5-nitrobenzene (2.16 g, 9.10 mmol), BINAP (0.95 g, 1.50 mmol) and Cs2CO3 (4.95 g, 15.20 mmol) in dioxane (10 mL) was added Pd(OAc)2 (0.34 g, 1.50 mmol), the mixture was stirred at 100 °C under N2 atmosphere for 16 hours. LC-MS was checked, and the reaction was completed. After the reaction, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether = 4% ~ 5%) to afford (S)-4-(3-chloro-5-nitrophenyl)-3-(methoxymethyl)morpholine (0.83 g, 36.8% yield) as a yellow solid. LCMS (ESI) calcd C12H16ClN2O4+[M + H]+m/z 287.08, found 286.9.
  • 7
  • [ 218595-25-6 ]
  • [ 2922565-87-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: iron; ammonium chloride / water; ethanol / 16 h / 80 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 25 °C / Inert atmosphere 4: boron tribromide / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
  • 8
  • [ 218595-25-6 ]
  • [ 2922566-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: iron; ammonium chloride / water; ethanol / 16 h / 80 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 25 °C / Inert atmosphere
  • 9
  • [ 218595-25-6 ]
  • [ 2922566-52-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: iron; ammonium chloride / water; ethanol / 16 h / 80 °C / Inert atmosphere
  • 10
  • [ 218595-25-6 ]
  • [ 2918200-71-0 ]
  • [ 2918200-84-5 ]
YieldReaction ConditionsOperation in experiment
48 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 0 - 20℃; 103 0453 Synthesis of 4-(2-chloro-4-fluorophenyl)-7-(((R)-1-((S)-3- (methoxymethyl)morpholino)-1-oxopropan-2-yl)oxy)isoquinolin-1(2H)-one, Example 103: To a stirred solution of (R)-2-((4-(2-chloro-4-fluorophenyl)-1-oxo-1,2- dihydroisoquinolin-7-yl)oxy)propanoic acid (Example 90, 60 mg, 0.2 mmol) in CH2Cl2 (9 mL) was added DIPEA (0.1 mL, 0.8 mmol) followed by (S)-3- (methoxymethyl)morpholine (35 mg, 0.2 mmol). The reaction mixture was cooled to 0°C, and T3P (0.14 mL, 0.2 mmol, 50 % in EtOAc) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by reverse phase prep-HPLC and lyophilized to afford 4-(2-chloro-4-fluorophenyl)-7-(((R)-1-((S)-3-(methoxymethyl)morpholino)-1- oxopropan-2-yl)oxy)isoquinolin-1(2H)-one (Example 103, 48 mg). LCMS (ESI) Calcd. for C24H24ClFN2O5: 474, found [M+H]+ = 475.1H NMR (400 MHz, DMSO-d6) δ 11.39 (br s, 1H), 7.66-7.59 (m, 2H), 7.50-7.45 (m, 1H), 7.36-7.24 (m, 2H), 7.00-6.90 (m, 2H), 5.50-5.33 (m, 1H), 4.37 (br s, 1H), 4.04 (br s, 2H), 3.85 (br s, 1H), 3.52 (br s, 1H), 3.41 (br s, 1H), 3.35-2.85 (m, 6H), 1.50-1.41 (m, 3H).
48 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 0 - 20℃; 103 0453 Synthesis of 4-(2-chloro-4-fluorophenyl)-7-(((R)-1-((S)-3- (methoxymethyl)morpholino)-1-oxopropan-2-yl)oxy)isoquinolin-1(2H)-one, Example 103: To a stirred solution of (R)-2-((4-(2-chloro-4-fluorophenyl)-1-oxo-1,2- dihydroisoquinolin-7-yl)oxy)propanoic acid (Example 90, 60 mg, 0.2 mmol) in CH2Cl2 (9 mL) was added DIPEA (0.1 mL, 0.8 mmol) followed by (S)-3- (methoxymethyl)morpholine (35 mg, 0.2 mmol). The reaction mixture was cooled to 0°C, and T3P (0.14 mL, 0.2 mmol, 50 % in EtOAc) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by reverse phase prep-HPLC and lyophilized to afford 4-(2-chloro-4-fluorophenyl)-7-(((R)-1-((S)-3-(methoxymethyl)morpholino)-1- oxopropan-2-yl)oxy)isoquinolin-1(2H)-one (Example 103, 48 mg). LCMS (ESI) Calcd. for C24H24ClFN2O5: 474, found [M+H]+ = 475.1H NMR (400 MHz, DMSO-d6) δ 11.39 (br s, 1H), 7.66-7.59 (m, 2H), 7.50-7.45 (m, 1H), 7.36-7.24 (m, 2H), 7.00-6.90 (m, 2H), 5.50-5.33 (m, 1H), 4.37 (br s, 1H), 4.04 (br s, 2H), 3.85 (br s, 1H), 3.52 (br s, 1H), 3.41 (br s, 1H), 3.35-2.85 (m, 6H), 1.50-1.41 (m, 3H).
 

Historical Records

Technical Information

Categories

Related Parent Nucleus of
[ 218595-25-6 ]

Morpholines

Chemical Structure| 211053-49-5

A180540 [211053-49-5]

(R)-3-Hydroxymethylmorpholine

Similarity: 1.00

Chemical Structure| 106910-83-2

A908640 [106910-83-2]

3-Hydroxymethylmorpholine

Similarity: 1.00

Chemical Structure| 211053-50-8

A293684 [211053-50-8]

(S)-Morpholin-3-ylmethanol

Similarity: 1.00

Chemical Structure| 955400-08-5

A118495 [955400-08-5]

3-(Methoxymethyl)morpholine hydrochloride

Similarity: 0.96

Chemical Structure| 218594-79-7

A314770 [218594-79-7]

(S)-Morpholin-3-ylmethanol hydrochloride

Similarity: 0.96