1232365-42-2|tert-Butyl (3,3-difluoro-1-(hydroxymethyl)cyclobutyl)carbamate| Ambeed

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Quality Control of [ 1232365-42-2 ] Purity: 97% SDS Specification

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Product Details of [ 1232365-42-2 ]

CAS No. :	1232365-42-2
Formula :	C₁₀H₁₇F₂NO₃
M.W :	237.24
SMILES Code :	O=C(OC(C)(C)C)NC1(CO)CC(F)(F)C1
MDL No. :	MFCD22566207
InChI Key :	RNZVBWMKWVRXIY-UHFFFAOYSA-N
Pubchem ID :	69928616

Safety of [ 1232365-42-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1232365-42-2 ]

* 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.

Downstream synthetic route of [ 1232365-42-2 ]

[ 1232365-42-2 ] Synthesis Path-Downstream 1~20

1
[ 1232365-41-1 ]
[ 1232365-42-2 ]

Yield	Reaction Conditions	Operation in experiment
91%		To a ice cooled solution of compound BB2-g (4 g ,0.0143 mol) in dry THF (100 mL) was slowly added a solution of 2M lithium boro hydride (30 mL) and the mixture was allowed to warm up to room temperature. The mixture was stirred for three hours at room temperature. Ice water and 5 % citric acid were added and the mixture was extracted three times with DCM. The organic phase was dried (Na2SO4), filtered and evaporated under reduced pressure which gave the title compound, (3.1 g, 91 %).
91%		Step h tert-Butyl 3.3-difluoro-l-(hydroxymethyncyclobutylcarbamate (BB2-hTo a ice cooled solution of compound BB2-g (4 g ,0.0143 mol) in dry THF (100 mL) was slowly added a solution of 2M lithium borohydride (30 mL) and the mixture was allowed to warm up to room temperature. The mixture was stirred for three hours at room temperature. Ice water and 5 % citric acid were added and the mixture was extracted three times with DCM. The organic phase was dried (Na2S04), filtered and evaporated under reduced pressure which gave the title compound. TLC system petroleum ether: ethyl acetate (1 : 1), RF = 0.3. Yield: 3.1 g, 91 %.
91%	With lithium borohydride; In tetrahydrofuran; at 20℃;Cooling with ice;	To a ice cooled solution of compound BB2-g (4 g ,0.0143 mol) in dry THF (100 mL) was slowly added a solution of 2M lithium borohydride (30 mL) and the mixture was allowed to warm up to room temperature. The mixture was stirred for three hours at room temperature. Ice water and 5 % citric acid were added and the mixture was extracted three times with DCM. The organic phase was dried (Na2S04), filtered and evaporated under reduced pressure which gave the title compound. TLC system petroleum ether: ethyl acetate (1 : 1), RF = 0.3. Yield: 3.1 g, 91 %.

91%		Step h tert-Butyl 3.3-difluoro-l-(hydroxymethyncyclobutylcarbamate (BB2-hTo a ice cooled solution of compound BB2-g (4 g , 0.0143 mol) in dry THF (100 mL) was slowly added a solution of 2M lithium borohydride (30 mL) and the mixture was allowed to warm up to room temperature. The mixture was stirred for three hours at room temperature. Ice water and 5 % citric acid were added and the mixture was extracted three times with DCM. The organic phase was dried (Na2S04), filtered and evaporated under reduced pressure which gave the title compound. TLC system petroleum ether: ethyl acetate (1 : 1), RF = 0.3. Yield: 3.1 g, 91 %.
91%		Step h) tert-Butyl 3,3-difluoro-1 -(hvdroxymethyl)cvclobutylcarbamate (BB2-h)To a ice cooled solution of compound BB2-g (4 g , 14.3 mmol) in dry THF (100 mL) was slowly added a solution of 2M lithium borohydride (30 mL) and the mixture was allowed to warm up to room temperature. The mixture was stirred for three hours at room temperature. Ice water and 5 % citric acid were added and the mixture was extracted three times with DCM. The organic phase was dried (Na2S04), filtered and evaporated under reduced pressure which gave the title compound (3.1 g, 91 %).
	With sodium tetrahydroborate; ethanol; for 16.0h;Reflux;	ethyl 1-((tert-butoxycarbonyl)amino)-3,3-difluorocyclobutyl-1-carboxylate (560mg, 2.01mmol) was suspended in ethanol (5mL), sodium borohydride(379mg, 10.02mmol) was added. The reaction solution was stirred at reflux for 16 hours, then evaporated todryness under reduced pressure to give a crude product. Water (10mL) and ethyl acetate (10mL) was added to thecrude product. The organic phase was separated and the aqueous phase was further extracted with ethyl acetate (10mL).The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated todryness under reduced pressure to give 332mg crude product as a yellow oil, which was used directly in the next step.

References: [1]Patent: WO2010/70615,2010,A1 .Location in patent: Page/Page column 28; 30.
[2]Patent: WO2011/70539,2011,A1 .Location in patent: Page/Page column 24; 26.
[3]Patent: WO2011/70541,2011,A1 .Location in patent: Page/Page column 25.
[4]Patent: WO2011/158197,2011,A1 .Location in patent: Page/Page column 31.
[5]Patent: WO2012/172473,2012,A1 .Location in patent: Page/Page column 22.
[6]Patent: EP3424928,2019,A1 .Location in patent: Paragraph 0301.

2
[ 1232365-42-2 ]
[ 1232365-43-3 ]

Yield	Reaction Conditions	Operation in experiment
88.5%	With Dess-Martin periodane; In dichloromethane; at 30℃;	To a solution of 1-(boc-amino)-3,3-difluorocyclobutane-1-methanol (3.42 g, 14.4 mmol) in DCM (100 mL) was added 1,1,1 -tris(acetoxy)- 1,1 -dihydro- 1 ,2-benziodoxol-3 (1 H)-one (7.34 g, 17.3 mmol) in few portions, (maintaining the temperature below 30C with water bathcooling). The mixture was poured into a stirred aqueous solution of Na2CO3 and Na2S2O3 and stirred until the organic phase became transparent (- 15 mm). The layers were separated and the aqueous layer was extracted with DCM (30 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give tert-butyl N-(3,3- difluoro-1-formylcyclobutyl)carbamate (3.16 g, 12.8 mmol, 88.5% yield) as light yellow solid.
87%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3.0h;	To a solution of compound BB2-h (3.1 g, 0.0130 mol) in dry DCM (100 mL) was added Dess Martin Period inane (19.9 g, 0.0470 mol) and the mixture was stirred for three hours at room temperature. Ethyl acetate (200 mL) was added and the organic phase was washed twice with 10 % sodium thiosulphate solution, twice with 0.5 M NaOH and with brine. The organic phase was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography with hexane/ethyl acetate as eluent which gave the title compound, (2.7 g, 87 %).
87%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3.0h;	Step Gamma) tert-Butyl 3.3-difluoro-l-formylcyclobutylcarbamate (BetaBeta2-Gamma)To a solution of compound BB2-h (3.1 g, 0.0130 mol) in dry DCM (100 mL) was added Dess Martin Period inane (19.9 g, 0.0470 mol) and the mixture was stirred for three hours at room temperature. Ethyl acetate (200 mL) was added and the organic phase was washed twice with 10 % sodium thiosulphate solution, twice with 0.5 M NaOH and with brine. The organic phase was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography with hexane/ethyl acetate as eluent which gave the title compound. TLC system; petroleum ether: ethyl acetate (1 : 1), RF = 0.4. Yield: 2.7 g, 87 %.

87%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3.0h;	To a solution of compound BB2-h (3.1 g, 0.0130 mol) in dry DCM (100 mL) was added Dess Martin Period inane (19.9 g, 0.0470 mol) and the mixture was stirred for three hours at room temperature. Ethyl acetate (200 mL) was added and the organic phase was washed twice with 10 % sodium thiosulphate solution, twice with 0.5 M NaOH and with brine. The organic phase was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography with hexane/ethyl acetate as eluent which gave the title compound. TLC system; petroleum ether: ethyl acetate (1 : 1), RF = 0.4. Yield: 2.7 g, 87 %.
87%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3.0h;	Step i) tert-Butyl 3,3-difluoro-l-formylcyclobutylcarbamate (BetaBeta2-Gamma) To a solution of compound BB2-h (3.1 g, 0.0130 mol) in dry DCM (100 mL) was added Dess Martin Period inane (19.9 g, 0.0470 mol) and the mixture was stirred for three hours at room temperature. Ethyl acetate (200 mL) was added and the organic phase was washed twice with 10 % sodium thiosulphate solution, twice with 0.5 M NaOH and with brine. The organic phase was dried and evaporated under reduced pressure. The residue was purified by silica gelchromatography with hexane/ethyl acetate as eluent which gave the title compound. TLC system; petroleum ether: ethyl acetate (1 : 1), RF = 0.4. Yield: 2.7 g, 87 %.
87%	With Dess-Martin periodane; In dichloromethane; at 20℃; for 3.0h;	Step i) tert-Butyl 3,3-difluoro-1 -formylcvclobutylcarbamate (BB2-QTo a solution of compound BB2-h (3.1 g, 0.0130 mol) in dry DCM (100 mL) was added Dess Martin Period inane (19.9 g, 0.0470 mol) and the mixture was stirred for three hours at room temperature. Ethyl acetate (200 mL) was added and the organic phase was washed twice with 10 % sodium thiosulphate solution, twice with 0.5 M NaOH and with brine. The organic phase was dried and evaporated under reduced pressure. The residue was purified by silica gel chromatography with hexane/ethyl acetate as eluent which gave the title compound (2.7 g, 87 %).

References: [1]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 85; 86.
[2]Patent: WO2010/70615,2010,A1 .Location in patent: Page/Page column 28; 30.
[3]Patent: WO2011/70539,2011,A1 .Location in patent: Page/Page column 24; 26.
[4]Patent: WO2011/70541,2011,A1 .Location in patent: Page/Page column 25.
[5]Patent: WO2011/158197,2011,A1 .Location in patent: Page/Page column 31.
[6]Patent: WO2012/172473,2012,A1 .Location in patent: Page/Page column 22.

3
[ 54166-15-3 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .
[4]Patent: WO2012/172473,2012,A1 .

4
[ 99974-66-0 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .
[4]Patent: WO2012/172473,2012,A1 .

5
[ 99173-61-2 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .
[4]Patent: WO2012/172473,2012,A1 .

6
[ 827032-79-1 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .
[4]Patent: WO2012/172473,2012,A1 .

7
[ 1232365-40-0 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/158197,2011,A1 .
[3]Patent: WO2012/172473,2012,A1 .

8
[ 1232365-42-2 ]
[ 1232365-44-4 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .

9
[ 1232365-42-2 ]
[ 1232365-45-5 ]

References: [1]Patent: WO2011/70539,2011,A1 .
[2]Patent: WO2011/70541,2011,A1 .
[3]Patent: WO2011/158197,2011,A1 .
[4]Patent: WO2012/172473,2012,A1 .

10
[ 1232365-42-2 ]
[ 1311321-33-1 ]

References: [1]Patent: WO2011/70541,2011,A1 .

11
[ 1232365-42-2 ]
[ 1352817-91-4 ]

References: [1]Patent: WO2011/158197,2011,A1 .

12
[ 129287-91-8 ]
[ 1232365-42-2 ]

References: [1]Patent: EP3424928,2019,A1 .

13
[ 1232365-42-2 ]
(x)C₂HF₃O₂*C₅H₉F₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 28℃; for 4.0h;	<strong>[1232365-42-2]tert-butyl (3,3-difluoro-1-(hydroxymethyl)cyclobutyl)carbamate</strong> (232mg, 0.98mmol) was dissolved in a mixed solvent of trifluoroacetic acid (0.3mL)and dichloromethane (2.7mL), the reaction solution was stirred at 28C for 4 hours, then evaporated to dryness underreduced pressure to give a crude product. Dichloromethane (10mL) was added to the crude product, and the solventwas evaporated under reduced pressure to give 350mg crude product as an orange oil which was a trifluoroacetate saltand used directly in the next step.

References: [1]Patent: EP3424928,2019,A1 .Location in patent: Paragraph 0302.

14
[ 1232365-42-2 ]
1-(3-cyano-4-((E)-dimethylaminomethyleneamino)phenyl)-3-(3,3-difluoro-1-(hydroxymethyl)cyclobutyl)thiourea [ No CAS ]

References: [1]Patent: EP3424928,2019,A1 .

15
[ 1232365-42-2 ]
(E)-N'-(2-cyano-4-(2,2-difluoro-7-oxa-5-azaspiro[3.4]oct-5-en-6-yl)aminophenyl)-N,N-dimethylformamidine [ No CAS ]

References: [1]Patent: EP3424928,2019,A1 .

16
[ 1232365-42-2 ]
N₄-(4-([1,2,4]triazolo[4,3-c]pyrimidin-7-yloxy)-3-methylphenyl)-N₆-(2,2-difluoro-7-oxa-5-azaspiro[3.4]oct-5-en-6-yl)quinazoline-4,6-diamine [ No CAS ]

References: [1]Patent: EP3424928,2019,A1 .

17
[ 1232365-42-2 ]
[ 74-88-4 ]
tert-butyl N-[3,3-difluoro-1-(methoxymethyl)cyclobutyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.3%	With silver(II) oxide; In dichloromethane; at 20℃;Darkness;	To a solution of <strong>[1232365-42-2]tert-butyl N-[3,3-difluoro-1-(hydroxymethyl)cyclobutyl]carbamate</strong> (940 mg, 3.96 mrnol) and iodomethane (7.88 g, 55.49 mmol, 3.45 mL) in DCM (100 mL) was added silver oxide (6.43 g, 27.75 mmol). The reaction flask was covered with aluminum foil (protect from light) and the mixture was stirred at r.t. The mixture was stirred at room temperature for 10 days, then filtered and concentrated under reduced pressure, to obtain tert-butyl N-[3,3-difluoro-1-(methoxymethyl)cyclobutyljcarbamate (1.01 g, 95.0% purity, 3.82 mmol, 96.3% yield) as white crystalline solid.

References: [1]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 87.

18
[ 1363380-83-9 ]
[ 1232365-42-2 ]

References: [1]Patent: WO2019/86141,2019,A1 .

19
methyl 1-[(tert-butoxy)carbonyl]amino-3,3-difluorocyclobutane-1-carboxylate [ No CAS ]
[ 1232365-42-2 ]

Yield	Reaction Conditions	Operation in experiment
99.3%	With methanol; sodium tetrahydroborate; In 1,2-dimethoxyethane; at 0 - 20℃; for 4.0h;	To a vigorously stirred solution of methyl 1-[(tert-butoxy)carbonyl]amino-3,3- difluorocyclobutane-1-carboxylate (3.85 g, 14.5 mmol) in dry dimethoxyethane (90 mL) and dry methanol (10 mL) at 0C was added portionwise sodium borohydride (1.10 g, 29.0 mmol). The mixture was stirred at 0C for 2 h, then warmed to r.t. and stirred for a further 2 h at ambienttemperature. The reaction was poured into stirred saturated aqueous Na2CO3 solution and extracted with MTBE (150 mL). The combined organic phases were washed with water (100 mL) and brine, dried over Na2SO4 and concentrated under reduced pressure to afford tert-butyl N-[3,3-difluoro-1-(hydroxymethyl)cyclobutyl]carbamate (3.42 g, 14.42 mmol, 99.3% yield) as white solid.

References: [1]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 85; 88; 89.

20
[ 1232365-42-2 ]
(1-amino-3,3-difluorocyclobutyl)methanol hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.5%	With hydrogenchloride; In 1,4-dioxane; at 20℃;	Tert-Butyl N- [3,3 -difluoro- 1 -(hydroxymethyl)cyclobutyl] carbamate (900 mg, 3.79mmol) was dissolved in 25 mL of 4M HC1/dioxane at r.t. and the resulting mixture was stirredovernight. Upon completion of the reaction (monitored by 1 H NMR), the resulting mixture was concentrated under reduced pressure, the residue was treated with 20 mL of acetonitrile, and filtered. The precipitate was washed with acetonitrile and dried in vacuo to obtain (1-amino-3,3- difluorocyclobutyl)methanol hydrochloride (550.0 mg, 3.17 mmol, 83.5% yield) as whitepowder.

References: [1]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 88; 89.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Appel Reaction • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Chugaev Reaction • Complex Metal Hydride Reductions • Corey-Kim Oxidation • Dess-Martin Oxidation • Ester Cleavage • Halogenation • Heat of Combustion • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Petasis Reaction • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Amines • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Swern Oxidation • Ugi Reaction

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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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

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CAS No.: 1232365-42-2

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CAS No.: 1232365-42-2

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Product Details of [ 1232365-42-2 ]

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Application In Synthesis of [ 1232365-42-2 ]

[ 1232365-42-2 ] Synthesis Path-Downstream 1~20

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