[ CAS No. 885277-59-8 ]

Name: 885277-59-8|tert-Butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate|97% GC
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CAS No. :	885277-59-8	MDL No. :	MFCD08059328
Formula :	C₁₁H₂₁NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VBQFMICMBHKUSL-UHFFFAOYSA-N
M.W :	231.29	Pubchem ID :	57355258
Synonyms :

Safety of [ 885277-59-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 885277-59-8 ]

* 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 [ 885277-59-8 ]
Downstream synthetic route of [ 885277-59-8 ]

[ 885277-59-8 ] Synthesis Path-Upstream 1~1

1
[ 885277-59-8 ]
[ 149771-43-7 ]

Reference： [1] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526

[ 885277-59-8 ] Synthesis Path-Downstream 1~18

1
[ 885277-59-8 ]
[ 149771-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: acetonitrile / Reflux

Reference： [1]Huang, Long Jiang; Teng, Da Wei [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526]

2
[ 885277-59-8 ]
[ 124-63-0 ]
[ 1279821-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃;

Reference： [1]Location in patent: experimental part Huang, Long Jiang; Teng, Da Wei [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526]

3
[ 92197-46-1 ]
[ 24424-99-5 ]
[ 885277-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; hydrogen In methanol at 40℃; for 4h;

Reference： [1]Location in patent: experimental part Huang, Long Jiang; Teng, Da Wei [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526]

4
[ 54221-37-3 ]
[ 885277-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: toluene / 4 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.08 h / 0 - 20 °C 3: palladium on activated charcoal; hydrogen / methanol / 4 h / 40 °C / 3102.97 Torr

Reference： [1]Huang, Long Jiang; Teng, Da Wei [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526]

5
[ 17740-40-8 ]
[ 885277-59-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.08 h / 0 - 20 °C 2: palladium on activated charcoal; hydrogen / methanol / 4 h / 40 °C / 3102.97 Torr

Reference： [1]Huang, Long Jiang; Teng, Da Wei [Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526]

6
[ 885277-59-8 ]
[ 98-59-9 ]
[ 1354947-77-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 18h;	26 Intermediate 26: 1 ,1-dimethylethyl 2-(hydroxymethyl)-5-([(4- methylphenyl)sulfonyl]oxy}methyl)-1 -pyrrolidinecarboxylate; To a solution of 1 ,1-dimethylethyl 2,5-bis(hydroxymethyl)-1 -pyrrolidinecarboxylate (commercially available, for example from J&W Pharmlab, 7.57g, 32.7 mmol) in dichloromethane (200 mL) was added triethylamine (4.79 mL, 34.4 mmol), 4- dimethylaminopyridine (0.20 g, 1.64 mmol) and p-toluenesulfonyl chloride (6.55 g, 34.4 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was diluted with DCM (200mL) and the solution washed with water (200mL). The organic layer was collected via a hydrophobic frit and the solvent removed under vacuum. The residue was purified by silica chromatography (Biotage SP4, eluting 30% EtOAc in iso-hexane (3 column volumes), a gradient from 30-50% (over 6 column volumes) then 50% EtOAc (3 column volumes)) to yield the title compound as a colourless gum (2.28g).1H NMR (400 MHz, Chloroform-d) δ ppm 1.39 (s, 9 H) 1.78 - 2.03 (m, 4 H) 2.45 (s, 3 H) 3.37 - 3.50 (m, 1 H) 3.62 - 3.71 (m, 1 H) 3.82 - 3.97 (m, 2 H) 3.99 - 4.09 (m, 2 H) 4.38 - 4.49 (m, 1 H) 7.36 (d, J=8.1 Hz, 2 H) 7.79 (d, J=8.3 Hz, 2 H)

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC; BIOGEN IDEC INC. - WO2012/4604, 2012, A1 Location in patent: Page/Page column 57

7
[ 885277-59-8 ]
1-(4-(7-(6-amino-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-((5-(methoxymethyl)-1-methylpyrrolidin-2-yl)methoxy)quinazolin-4-yl)piperazin-1-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 25 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C 2.2: 2 h / 25 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 40 °C 3.2: 2 h / 40 °C 4.1: trifluoroacetic acid / 2 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -78 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/97537, 2020, A2

8
[ 885277-59-8 ]
[ 89855-52-7 ]

Yield	Reaction Conditions	Operation in experiment
53.1%	With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 8h;	80.1 Step 1: (1 -methy lpy rrolidine-2,5 -diy l)dimethanol [0800] A solution of tert-butyl 2,5-bis(hydroxymethyl)pyrrolidine-l-carboxylate (1500.0 mg, 6.49 mmol) and lithium aluminum hydride (369.0 mg, 9.72 mmol) in tetrahydrofuran (60 mL) was stirred at 25 °C for 8 hours. Upon completion, the reaction was concentrated. The residue was purified by flash chromatography on silica gel eluting with methanol/dichloromethane (1 :4) to afford (l-methylpyrrolidine-2,5-diyl)dimethanol (500 mg, 3.44 mmol, 53.1% yield) as a colorless oil. LC-MS: (ESI, m/z): 146.2 [M+H]+

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/97537, 2020, A2 Location in patent: Paragraph 0800

9
[ 885277-59-8 ]
tert-butyl 4-(7-(6-(bis(4-methoxybenzyl)amino)-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-((5-(hydroxymethyl)-1-methylpyrrolidin-2-yl)methoxy)quinazolin-4-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 25 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C 2.2: 2 h / 25 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/97537, 2020, A2

10
[ 885277-59-8 ]
tert-butyl 4-(7-(6-(bis(4-methoxybenzyl)amino)-3-(trifluoromethyl)pyridin-2-yl)-6-chloro-2-((5-(methoxymethyl)-1-methylpyrrolidin-2-yl)methoxy)quinazolin-4-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 25 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C 2.2: 2 h / 25 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 40 °C 3.2: 2 h / 40 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/97537, 2020, A2

11
[ 885277-59-8 ]
6-(6-chloro-2-((5-(methoxymethyl)-1-methylpyrrolidin-2-yl)methoxy)-4-(piperazin-1-yl)quinazolin-7-yl)-5-(trifluoromethyl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / 25 °C 2.1: sodium hydride / tetrahydrofuran / 0.17 h / 25 °C 2.2: 2 h / 25 °C 3.1: sodium hydride / tetrahydrofuran / 0.08 h / 40 °C 3.2: 2 h / 40 °C 4.1: trifluoroacetic acid / 2 h / 50 °C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2020/97537, 2020, A2

12
[ 885277-59-8 ]
[ 115262-01-6 ]
2,5-di((difluoromethoxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium acetate In dichloromethane; water at 20℃; for 12h;	132.2 Step 2: 2,5-Bis((difluoromethoxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1.50g, 6.50mmol) was dissolved in DCM (5mL), KOAc (7.40g, 75.00mmol) and H2O( 5mL), then add (bromo(difluoro)methyl)-trimethylsilane (7.80mL, 50.00mmol), and react at room temperature for 12h. The reaction was quenched with water, extracted with DCM (30ml×2), the organic phases were combined, dried with anhydrous Na2SO4, filtered, concentrated and separated by silica gel column chromatography (eluent: PE/EtOAc(v/v)=5/1) , A colorless liquid (2.10g, 98%) was obtained.

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A Location in patent: Paragraph 1462; 1467-1469

13
[ 885277-59-8 ]
2,5-di((difluoromethoxy)methyl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate / dichloromethane; water / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A

14
[ 885277-59-8 ]
4-(2,5-di((difluoromethoxy)methyl)pyrrolidin-1-yl)benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium acetate / dichloromethane; water / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; ruphos / dichloromethane / 12 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A

15
[ 885277-59-8 ]
4-(2,5-di((difluoromethoxy)methyl)pyrrolidin-1-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium acetate / dichloromethane; water / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; ruphos / dichloromethane / 12 h / 110 °C / Inert atmosphere 4: water; lithium hydroxide; methanol / 24 h / 20 °C

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A

16
[ 885277-59-8 ]
4-(2,5-di((difluoromethoxy)methyl)pyrrolidin-1-yl)-N-((S)-2-cyano-1-(4-(ethylsulfonyl)phenyl)ethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium acetate / dichloromethane; water / 12 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; ruphos / dichloromethane / 12 h / 110 °C / Inert atmosphere 4: water; lithium hydroxide; methanol / 24 h / 20 °C 5: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 12 h / 20 °C

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A

17
diethyl N-tert-butyloxycarbonyl-2,5-pyrrole dicarboxylate [ No CAS ]
[ 885277-59-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With lithium borohydride In tetrahydrofuran at -10 - 20℃; for 4h;	132.1 Step 1: 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester Dissolve tert-butyl 2,5-bis(ethoxyformyl)pyrrolidine-1-carboxylate (2.0g, 6.30mmol) in THF (10mL), cool to -10°C, add LiBH4 (0.28g, 13.00mmol), warmed to room temperature and reacted for 4h. The reaction was quenched by adding water, extracted with EtOAc (30ml×2), the organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated to obtain a colorless oily liquid (1.50g, 99%).

Reference： [1]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN113072542, 2021, A Location in patent: Paragraph 1462; 1464-1466

18
C₁₁H₁₃NO₄ [ No CAS ]
[ 885277-59-8 ]

Yield	Reaction Conditions	Operation in experiment
97.5%	With hydrogen; sodium carbonate In ethanol; water at 100℃; for 5h; Autoclave;	4 Dissolve 10g of compound 3a in 400mL of ethanol, add it to the autoclave, and then add 3g of RaneyNi and 10mL of saturated sodium carbonate aqueous solution in sequence to replace the gas,After evacuating the autoclave into a vacuum, fill the autoclave with H2 until the partial pressure of H2 in the autoclave is 0.2Mpa, stir and react at 100 for 5h, filter with diatomaceous earth, take the filtrate, wash with water, concentrate under reduced pressure, fast column Chromatography yielded 10.1 g of compound 2 with a separation yield of 97.5%.

Reference： [1]Current Patent Assignee: SHANGHAI LINGFU PHARMACEUTICAL RES - CN113563243, 2021, A Location in patent: Paragraph 0078-0092

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H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 885277-59-8 ]

Quality Control of [ 885277-59-8 ]

Related Doc. of [ 885277-59-8 ]

Product Details of [ 885277-59-8 ]

Safety of [ 885277-59-8 ]

Application In Synthesis of [ 885277-59-8 ]

[ 885277-59-8 ] Synthesis Path-Upstream 1~1

[ 885277-59-8 ] Synthesis Path-Downstream 1~18

Related Functional Groups of [ 885277-59-8 ]

Alcohols

Amides

Related Parent Nucleus of [ 885277-59-8 ]

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 885277-59-8 ]

Related Parent Nucleus of
[ 885277-59-8 ]