Spiro[indoline-3,3'-pyrrolidin]-2-one

Base Information

• Chemical Name: Spiro[indoline-3,3'-pyrrolidin]-2-one
• CAS No.: 6786-41-0
• Molecular Formula: C11H12N2O
• Molecular Weight: 188.229
• DSSTox Substance ID: DTXSID50449607
• Nikkaji Number: J946.472G
• ChEMBL ID: CHEMBL4589849
• Mol file: 6786-41-0.mol

Synonyms:spiro[indoline-3,3'-pyrrolidin]-2-one;6786-41-0;1,2-dihydrospiro[indole-3,3'-pyrrolidine]-2-one;Spiro[1H-indole-3,3'-pyrrolidine]-2-one;spiro[indole-3,3'-pyrrolidin]-2(1H)-one;SCHEMBL251170;CHEMBL4589849;DTXSID50449607;FQSHLSLQUHZOMV-UHFFFAOYSA-N;spiro(oxindole-3,3'-pyrrolidine);AMY34248;AKOS022171512;SB11806;AS-34017;Spiro[indoline-3,3'-pyrrolidine]-2-one;CS-0007691;A867173

Chemical Property of Spiro[indoline-3,3'-pyrrolidin]-2-one

Chemical Property:

• Density: 1.27
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 188.094963011
• Heavy Atom Count: 14
• Complexity: 266

Purity/Quality:

97% ^*data from raw suppliers

Spiro[indole-3,3''-pyrrolidin]-2(1H)-oneHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC12C3=CC=CC=C3NC2=O

Technology Process of Spiro[indoline-3,3'-pyrrolidin]-2-one

There total 2 articles about Spiro[indoline-3,3'-pyrrolidin]-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 47.0%

1,2,3,4-tetrahydro-β-carbolin-9-ol (260550-30-9) → betacarboline (244-63-3) + 3,4-dihydro-β-carboline (4894-26-2) + spiro[indole-3,3'-pyrrolidin]-2(1H)-one (6786-41-0)

Guidance literature:

With hydrogenchloride; In methanol; water; for 3h; Heating;

DOI:10.3987/COM-99-8743

Reference yield:

benzyl 4-oxo-1-piperidinecarboxylate (19099-93-5) → spiro[indole-3,3'-pyrrolidin]-2(1H)-one (6786-41-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 2 h / -78 - 20 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 °C

3.1: 84 percent / NMO / OsO₄ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating

4.1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 °C

5.1: 88 percent / Jones reagent / acetone / 0.17 h / at ice bath

6.1: DCC / tetrahydrofuran / 6 h / Heating

7.1: t-BuOCl / CH₂Cl₂ / 10 h / 20 °C / Heating; in dark

7.2: Zn(OAc)2 / nitromethane / 1 h / 20 °C

8.1: H₂ / 10 percent Pd-C / methanol / 40 h / 20 °C

With N-methyl-2-indolinone; jones reagent; tert-butylhypochlorite; boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2005.10.015

Reference yield: 36.8%

di-tert-butyl dicarbonate (24424-99-5) + spiro[indole-3,3'-pyrrolidin]-2(1H)-one (6786-41-0) → tert-butyl 2-oxospiro[indoline-3,3’-pyrrolidine]-1'-carboxylate (205383-87-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/acsmedchemlett.7b00418

upstream raw materials:

1,2,3,4-tetrahydro-β-carbolin-9-ol

benzyl 4-oxo-1-piperidinecarboxylate

Downstream raw materials:

tert-butyl 2-oxospiro[indoline-3,3’-pyrrolidine]-1'-carboxylate