[ CAS No. 788812-21-5 ]

Name: 788812-21-5|Spiro[isoindoline-1,4'-piperidin]-3-one|98%
Brand: Ambeed
SKU: A569366
Rating: 91 (25 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 788812-21-5

Structure of 788812-21-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 788812-21-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 788812-21-5 ]

SDS Specification

Alternatived Products of [ 788812-21-5 ]

Product Details of [ 788812-21-5 ]

CAS No. :	788812-21-5	MDL No. :	MFCD22058263
Formula :	C₁₂H₁₄N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JKJBINGBZKSOFX-UHFFFAOYSA-N
M.W :	202.25	Pubchem ID :	15548169
Synonyms :

Safety of [ 788812-21-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P342+P311-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 788812-21-5 ]

* 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 [ 788812-21-5 ]

[ 788812-21-5 ] Synthesis Path-Downstream 1~19

1
[ 209160-93-0 ]
[ 788812-21-5 ]
1'-(3-((S)-(3-Chlorophenyl))-4-(N-(phenylsulfonyl)(methylamino))butyl)-spiro(1-oxoisoindoline-3,4'-piperidine) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2469 - 2473

2
[ 19926-90-0 ]
[ 788812-21-5 ]
1'-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)spiro[isoindoline-1,4'-piperidin]-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 6h;	EXAMPLE 3; l'-(bicyclo[2.2.1]hept-S-en-2-ylmethyl)spiro[isoindoline-l,4'-piperidin]-3- one (Compound No. 267); EPO <DP n="75"/> Compound No. 267[00209] Sodium triacetoxyborohydride (31 mg, 0.15 mmol) was added to a stirred solution of spiro[isoindoline-l,4'-piperidin]-3-one 3a (20 mg, 0.10 mmol) and bicyclo[2.2.1]hept-5- ene-2-carbaldehyde (18mg, 0.15mmol) in 1,2-dichloroethane (1 mL) and the mixture was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the crude product was purified by preparative HPLC (5-70% CH3CN-H2O gradient withθ.05% TFA, 15 min) to give compound no. 267.

Reference： [1]Patent: WO2006/58303,2006,A2 .Location in patent: Page/Page column 73-74

3
[ 920023-54-7 ]
[ 788812-21-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 0.10 g (0.33 mmol) tert-butyl 3-oxo-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidine]-1'-carboxylate in 3.3 ml dichloromethane were added 0.25 ml (3.3 mmol) trifluoroacetic acid at room temperature. After stirring for 4 h the reaction mixture was diluted with 20 ml aqueous 1 M sodium hydroxide solution (20 ml) and extracted with ethyl acetate (3*50 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (0.095 g) as a light yellow solid. MS m/e (%): 203 (M+H+, 100).

Reference： [1]Patent: US2007/27173,2007,A1 .Location in patent: Page/Page column 116-117

4
[ 788812-21-5 ]
1'-[(6-chloro-1H-indol-3-yl)carbonyl]spiro[isoindole-1,4'-piperidin]-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%		To a solution of 0.060 g (0.31 mmol) 6-chloro-1H-indole-3-carboxylic acid in 3 ml dichloromethane were added 0.045 ml (0.38 mmol) 1-chloro-N,N,2-trimethyl-propenylamine at room temperature. After stirring for 1 h the reaction mixture was concentrated in vacuo. The residue was redissolved in 2 ml dry N,N-dimethylformamide. A solution of 0.062 g (0.31 mmol) <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> and 0.064 ml (0.46 mmol) triethylamine in 1 ml dry N,N-dimethylformamide was added at room temperature. After stirring for 2 h the reaction mixture was quenched with 1 M aqueous sodium hydroxide solution (30 ml) and extracted with ethyl acetate (350 ml). The combined organic layers were washed with water (230 ml), 0.5 M aqueous hydrochloric acid solution (130 ml) and brine (130 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was triturated in warm diethyl ether, filtrated and dried in vacuo to give the title compound (0.031 g, 22%) as light brown solid with a purity of approx. 80% by LC-.MS. MS m/e (%): 378 (M-H+, 100).

Reference： [1]Patent: US2007/27173,2007,A1 .Location in patent: Page/Page column 115; 117

5
[ 920023-68-3 ]
[ 788812-21-5 ]
2-{6-chloro-3-[(3-oxo-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidin]-1'-yl)carbonyl]-1H-indol-1-yl}-N-methylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	To a solution of 0.35 g (0.13 mmol) 6-chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acid, 0.025 ml (0.14 mmol) N,N-diisopropylethylamine and 0.055 g (0.14 mmol) 0-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate in 2 ml dry N,N-dimethylformamide were added 0.029 g (0.14 mmol) <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> at room temperature. After stirring for 2 h the reaction mixture was quenched with 0.5 M aqueous sodium hydroxide solution (20 ml) and extracted with ethyl acetate (230 ml). The combined organic layers were washed with water (230 ml) and brine (1*30 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (aminopropyl-modified silica gel, dichloromethane/methanol) to give the title compound (0.026 g, 44%) as a white solid. MS m/e (%): 451 (M+H+, 100).

Reference： [1]Patent: US2007/27173,2007,A1 .Location in patent: Page/Page column 117

6
[ 2131-55-7 ]
[ 788812-21-5 ]
[ 915104-42-6 ]

Yield	Reaction Conditions	Operation in experiment
70%		Preparation 3: N-(4-Chlorophenyl)-3-oxo-2,3-dihydro-1'H-spiro[isoindole-1 ,4'-piperidine]-1'- carbothioamide. The title compound was prepared from <strong>[788812-21-5]spiro[isoindole-1,4'-piperidin]-3(2H)-one</strong> (WO 01/45707, p 83) and 4-chlorophenyl isothiocyanate, using the same method as that described for preparation 1, in 70% yield.1HNMR(400MHz, DMSO-d6) δ: 1.72-1.86(m, 4H), 4.17-4.29(m, 4H), 6.82(d, 1 H), 6.95(m, 1 H), 7.18(m, 1 H), 7.31 (m, 4H), 7.46(d, 1 H), 9.41 (s, 1H),10.45(s, 1 H); LRMS APCI m/z 372 [M+H]+.

Reference： [1]Patent: WO2006/123242,2006,A1 .Location in patent: Page/Page column 29

7
[ 936691-71-3 ]
[ 788812-21-5 ]
N-methyl-3-oxo-N-(2-piperidin-1-ylethyl)-2,3-dihydro-1'H-spiro[isoindole-1,4'-piperidine]-1'-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5101 - 5106

8
[ 268538-11-0 ]
[ 788812-21-5 ]
3-oxo-N-(5-phenyl-2-pyrazinyl)spiro[isoindoline-1.4'-piperidine]-1'-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3511 - 3516

9
[ 24424-99-5 ]
[ 788812-21-5 ]
[ 920023-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; acetonitrile; for 3h;	Step 2; Crude <strong>[788812-21-5]spiro[isoindoline-1,4'-piperidin]-3-one</strong> was dissolved in 1:1 MeCN:10% aq K2CO3 (20 mL) and Boc2O (50 mg, 0.23 mmol, 2.0 equiv) added. The mixture stirred for 3 h. The solution was evaporated and the mixture was diluted with EtOAc. The organic layer was washed with 1.0 M aq HCl and brine, dried over Na2SO4, and evaporated. The residue was purified by flash chromatography on silica, eluting with 20-80% EtOAc in hexanes to afford tert-butyl 3-oxospiro[isoindoline-1,4'-piperidine]-1'-carboxylate.

Reference： [1]Patent: US2019/270744,2019,A1 .Location in patent: Paragraph 0290; 0291
[2]Patent: US2011/34455,2011,A1 .Location in patent: Page/Page column 38

10
[ 1017540-78-1 ]
[ 788812-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; at 75℃; for 19h;	Step 1; Tert-butyl 2-(4-methoxybenzyl)-3-oxospiro[isoindoline-1,4'-piperidine]-1'-carboxylate (50 mg, 0.12 mmol, 1.0 equiv) and TFA (7 mL) were heated to 75 C. for 19 h. After this time LC-MS showed removal of the Boc- and p-methoxybenzyl groups. The mixture was concentrated to leave crude spiro[isoindoline-1,4'-piperidin]-3-one which was used directly.

Reference： [1]Patent: US2011/34455,2011,A1 .Location in patent: Page/Page column 38

11
2’,3’-dihydro-1‘H-spiro[isoindole-1,4’-pyridin]-3(2H)-one [ No CAS ]
[ 788812-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at 0 - 20℃; for 3h;	NaBH(OAc)3 (856 mg, 4.05 mmol) was added to a 0 C cooled suspension of the compound obtained in step c (326 mg, 1.62 mmol) and AcOH (5 mL) in ACN (5 mL). The reaction mixture was allowed to reach r.t., stirred at this temperature for 3 h and slowly poured into NaHCO3 (saturated aqueous solution, 20 mL). The mixture was taken up to pH 8-9 with NaOH (36% aqueous solution) and extracted with DCM (5x20 mL) and n-BuOH (2x15 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated, to give the title compound as an off-white solid (360 mg,quantitative yield). The crude residue was submitted to next step without purification.HPLC-MS (Method Bi): Ret, 5.61 mm; ESl-MS m/z, 203.1 (M+1).

Reference： [1]Patent: WO2016/78770,2016,A1 .Location in patent: Page/Page column 181; 182

12
[ 788812-21-5 ]
2-(3-oxospiro[isoindoline-1,4'-piperidin]-1'-yl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 3407 - 3427

13
[ 4023-02-3 ]
[ 788812-21-5 ]
C₁₃H₁₆N₄O [ No CAS ]