1262396-32-6|(S)-6-(tert-Butoxycarbonyl)-6-azaspiro[2.5]octane-5-carboxylic acid| Ambeed

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Quality Control of [ 1262396-32-6 ] Purity: 98% SDS Specification

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Product Details of [ 1262396-32-6 ]

CAS No. :	1262396-32-6
Formula :	C₁₃H₂₁NO₄
M.W :	255.31
SMILES Code :	O=C([C@@H](N(C(OC(C)(C)C)=O)CC1)CC21CC2)O
MDL No. :	MFCD28955658
InChI Key :	PJVQCWIKEOHTOE-VIFPVBQESA-N
Pubchem ID :	66848235

Safety of [ 1262396-32-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P201-P202-P261-P272-P280-P302+P352-P308+P313-P333+P313-P405-P501

Application In Synthesis of [ 1262396-32-6 ]

* 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 [ 1262396-32-6 ]

[ 1262396-32-6 ] Synthesis Path-Downstream 1~19

1
[ 1262396-27-9 ]
[ 1262396-32-6 ]

References: [1]Patent: WO2011/6960,2011,A1 .

2
[ 1262396-30-4 ]
[ 1262396-32-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Pd-BaSO4; In methanol; at 20℃;	Example 16: Preparation of intermediate 17: (S)-6-aza-spiror2.51octane-5,6- dicarboxylic acid 6-tert-butyl esterTo a solution of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 5-benzyl ester 6- tert-butyl ester (intermediate 16, 1 1 Og, 0.32mol , ee:66%) in anhydrous methanol(1 L) was added Pd/BaSO4 (5Og) under hydrogen, the reaction mixture was stirred at room temperature for overnight. The resulting mixture was filtered and the liquid phase was evaporated to give 68g of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6-tert-butyl ester (light white solid, yield:85%) which was recrystallized with PE/EtOAc (4:1 ) to give 38g of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6- tert-butyl ester.1HNMR (CDCI3) d ppm 12.67 (s, 1 H), 4.60 (m, 2H), 3.85 (m, 1 H), 3.10 (m, 1 H), 2.08 (m, 1 H), 1.79 (m, 1 H), 1.40 (d, 9H), 0.84 (m, 1 H), 0.28-0.32 (m, 4H)

References: [1]Patent: WO2011/6960,2011,A1 .Location in patent: Page/Page column 34.

3
[ 1262396-32-6 ]
[ 1262396-67-7 ]

References: [1]Patent: WO2011/6960,2011,A1 .

4
[ 1262396-32-6 ]
[ 1262396-90-6 ]

References: [1]Patent: WO2011/6960,2011,A1 .

5
[ 1262396-32-6 ]
[ 1262395-09-4 ]

References: [1]Patent: WO2011/6960,2011,A1 .

6
[ 1262396-32-6 ]
[ 1262395-87-8 ]

References: [1]Patent: WO2011/6960,2011,A1 .

7
[ 1262396-32-6 ]
[ 1262396-34-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With borane-THF; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere;Conversion of starting material;	Example 17: Preparation of intermediate 18: (S)-5-hvdroxymethyl-6-aza- spiro[2.51octane-6- carboxylic acid tert-butyl esterTo a solution of (S)-6-aza-spiro[2.5]octane-5,6-dicarboxylic acid 6-tert-butyl ester (intermediate 17, 35g, 0.122mol ) in anhydrous THF (300ml) was added BH3/THF (1 M, 360ml, 0.365mol) under nitrogen at 0 C. After the addition was completed, the reaction mixture was warmed to room temperature and stirred at room temperature for overnight. The resulting mixture was evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether/ethyl acetate from 10/1 to 5/1 ). (S)-5-Hydroxymethyl-6-aza-spiro[2.5]octane-6-carboxylic acid tert- butyl ester was obtained as colourless oil (31 g), yield:86%.1HNMR (CDCI3) d ppm 4.40 (m, 1 H), 4.01 (m, 1 H), 3.66 (m, 1 H), 3.06 (m, 1 H), 2.03 (m, 1 H), 1.87 (m, 1 H), 1.50 (s, 9H), 1.02 (d, 1 H), 0.85 (d, 1 H), 0.27-0.43 (m, 4H);MS Calcd.: 241 ; MS Found: 142 ([M-100+1 ]+).

References: [1]Patent: WO2011/6960,2011,A1 .Location in patent: Page/Page column 34-35.

8
[ 1262396-32-6 ]
[ 1262396-36-0 ]

References: [1]Patent: WO2011/6960,2011,A1 .

9
[ 1262396-32-6 ]
[ 1262396-38-2 ]

References: [1]Patent: WO2011/6960,2011,A1 .

10
[ 1262396-32-6 ]
C₁₈H₂₄ClN₃O₂ [ No CAS ]

References: [1]Patent: WO2011/6960,2011,A1 .

11
[ 1262396-32-6 ]
[ 1262396-48-4 ]

References: [1]Patent: WO2011/6960,2011,A1 .

12
[ 1262396-32-6 ]
[ 1262396-51-9 ]

References: [1]Patent: WO2011/6960,2011,A1 .

13
[ 1262396-32-6 ]
[ 1262396-53-1 ]

References: [1]Patent: WO2011/6960,2011,A1 .

14
[ 1262396-32-6 ]
methyl (2S)-2-amino-3-[(3S)-2-oxopyrrolidin-3-yl]propanoate hydrochloride [ No CAS ]
(S)-tert-butyl 5-(((S)-1-methoxy-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)-6-azaspiro[2.5]octane-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In N,N-dimethyl-formamide; at 25℃; for 1.0h;	A mixture of methyl (2S)-2-amino-3-[(3S)-2-oxopyrrolidin-3-yl]propanoate (230 mg, 1.03 mmol, 1 eq, HCl), <strong>[1262396-32-6](7S)-6-tert-butoxycarbonyl-6-azaspiro[2.5]octane-7-carboxylic acid</strong> (263.72 mg, 1.03 mmol, 1 eq), T3P (657.31 mg, 2.07 mmol, 614.31 uL, 2 eq), Et3N (522.60 mg, 5.16 mmol, 718.85 uL, 5 eq) and DMF (5 mL) was stirred at 25 C. for 1 h. The reaction mixture was diluted with H2O (30 mL) and extracted with DCM (30 mL*3). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/EtOAc=0/1) to get the product (S)-tert-butyl 5-(((S)-1-methoxy-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)-6-azaspiro[2.5]octane-6-carboxylate (300 mg, 708.38 umol, 68.58% yield), as yellow oil. MS (ESI) m/z 424.1 [M+H]+
300 mg	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In N,N-dimethyl-formamide; at 25℃; for 1.0h;	A mixture of methyl (2S)-2-amino-3-[(3S)-2-oxopyrrolidin-3-yl]propanoate (230 mg, 1.03 mmol, 1 eq, HCl), <strong>[1262396-32-6](7S)-6-tert-butoxycarbonyl-6-azaspiro[2.5]octane-7-carboxylic acid</strong> (263.72 mg, 1.03 mmol, 1 eq), T3P (657.31 mg, 2.07 mmol, 614.31 uL, 2 eq), Et3N (522.60 mg, 5.16 mmol, 718.85 uL, 5 eq) and DMF (5 mL) was stirred at 25 C. for 1 h. The reaction mixture was diluted with H2O (30 mL) and extracted with DCM (30 mL*3). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/EtOAc=0/1) to get the product (S)-tert-butyl 5-(((S)-1-methoxy-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamoyl)-6-azaspiro[2.5]octane-6-carboxylate (300 mg, 708.38 umol, 68.58% yield), as yellow oil. MS (ESI) m/z 424.1 [M+H]+

References: [1]Patent: US11124497,2021,B1 .Location in patent: Page/Page column 450-452.
[2]Patent: US11124497,2021,B1 .Location in patent: Page/Page column 450-452.

15
[ 1262396-32-6 ]
(2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With Adams’s catalyst; hydrogen; acetic acid; In ethyl acetate; at 20℃; under 2280.15 Torr;	To a solution of (5S)-6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5- carboxyic acid (250 mg, 0.98 mmol, 1.0 eq.) in EA (3 mL) and acetic acid (3 mL) was added PtO?. (178 mg, 0.78 mmol, 0.8 eq.). Hydrogen (3atm) was introduced. The mixture was stirred overnight at rt. The mixture was filtered, and the filtrate was collected and concentrated under reduced pressure. The residue was chromatographed on a Cl 8 column with MeCN: water (2:3) to provide (2S)-l-(tert-butoxycarhonyl)-4.,4-dimethylpiperidine-2- carboxylic add (180mg, 61%) as a white solid. LCMS (ESI, /z): 258 [M+H]L
61%	With Adams’s catalyst; hydrogen; acetic acid; In ethyl acetate; at 20℃; under 2280.15 Torr;	To a solution of (5S)-6-(tert-butoxycarbonyl)-6-azaspiro[2.5]octane-5- carboxyic acid (250 mg, 0.98 mmol, 1.0 eq.) in EA (3 mL) and acetic acid (3 mL) was added PtO?. (178 mg, 0.78 mmol, 0.8 eq.). Hydrogen (3atm) was introduced. The mixture was stirred overnight at rt. The mixture was filtered, and the filtrate was collected and concentrated under reduced pressure. The residue was chromatographed on a Cl 8 column with MeCN: water (2:3) to provide (2S)-l-(tert-butoxycarhonyl)-4.,4-dimethylpiperidine-2- carboxylic add (180mg, 61%) as a white solid. LCMS (ESI, /z): 258 [M+H]L

References: [1]Patent: WO2021/252491,2021,A1 .Location in patent: Paragraph 0246.
[2]Patent: WO2021/252491,2021,A1 .Location in patent: Paragraph 0246.

16
[ 1262396-32-6 ]
tert-butyl (2S)-2-(((2S)-4-(benzylamino)-3-hydroxy-4-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)carbamoyl)-4,4-dimethylpiperidine-1-carboxylate [ No CAS ]

References: [1]Patent: WO2021/252491,2021,A1 .

17
[ 1262396-32-6 ]
(2S)-N-((2S)-4-(benzylamino)-3-hydroxy-4-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)-4,4-dimethylpiperidine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2021/252491,2021,A1 .

18
[ 1262396-32-6 ]
(2S)-N-((2S)-4-(benzylamino)-3-hydroxy-4-oxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)-1-(1H-indole-2-carbonyl)-4,4-dimethylpiperidine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2021/252491,2021,A1 .

19
[ 1262396-32-6 ]
(2S)-N-(4-(benzylamino)-3,4-dioxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)-1-(1H-indole-2-carbonyl)-4,4-dimethylpiperidine-2-carboxamide [ No CAS ]

References: [1]Patent: WO2021/252491,2021,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Arndt-Eistert Homologation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Halogenation • Heat of Combustion • Hunsdiecker-Borodin Reaction • Hydride Reductions • Lawesson's Reagent • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 1262396-32-6 ]

Amides

A274497 [1373028-01-3]

5-(tert-Butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid

Similarity: 0.98

A264794 [187752-72-3]

cis-1-(tert-Butoxycarbonyl)-4-methylpiperidine-2-carboxylic acid

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A578231 [1262408-54-7]

1-(tert-Butoxycarbonyl)-4-methylpiperidine-2-carboxylic acid

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A660227 [1255664-97-1]

1-(tert-Butoxycarbonyl)-4-isopropylpiperidine-2-carboxylic acid

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A117728 [197142-34-0]

(1R,3S,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid

Similarity: 0.97

Carboxylic Acids

A988988 [1417743-24-8]

6-[(tert-Butoxy)carbonyl]-6-azaspiro[2.5]octane-5-carboxylic acid

Similarity: 1.00

A274497 [1373028-01-3]

5-(tert-Butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid

Similarity: 0.98

A578231 [1262408-54-7]

1-(tert-Butoxycarbonyl)-4-methylpiperidine-2-carboxylic acid

Similarity: 0.98

A660227 [1255664-97-1]

1-(tert-Butoxycarbonyl)-4-isopropylpiperidine-2-carboxylic acid

Similarity: 0.98

A992900 [155302-06-0]

1-(tert-Butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid

Similarity: 0.98

Related Parent Nucleus of
[ 1262396-32-6 ]

Piperidines

A274497 [1373028-01-3]

5-(tert-Butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid

Similarity: 0.98

A264794 [187752-72-3]

cis-1-(tert-Butoxycarbonyl)-4-methylpiperidine-2-carboxylic acid

Similarity: 0.98

A578231 [1262408-54-7]

1-(tert-Butoxycarbonyl)-4-methylpiperidine-2-carboxylic acid

Similarity: 0.98

A660227 [1255664-97-1]

1-(tert-Butoxycarbonyl)-4-isopropylpiperidine-2-carboxylic acid

Similarity: 0.98

A992900 [155302-06-0]

1-(tert-Butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid

Similarity: 0.98

Spiroes

A988988 [1417743-24-8]

6-[(tert-Butoxy)carbonyl]-6-azaspiro[2.5]octane-5-carboxylic acid

Similarity: 1.00

A274497 [1373028-01-3]

5-(tert-Butoxycarbonyl)-5-azaspiro[2.5]octane-6-carboxylic acid

Similarity: 0.98

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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.: 1262396-32-6

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