tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate

Base Information

• Chemical Name: tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate
• CAS No.: 690632-05-4
• Molecular Formula: C₁₇H₂₁BrN₂O₄
• Molecular Weight: 397.269
• Hs Code.: 2933399990
• European Community (EC) Number: 800-956-6
• DSSTox Substance ID: DTXSID80383388
• Wikidata: Q82175080
• Mol file: 690632-05-4.mol

Synonyms:690632-05-4;tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate;tert-butyl 6-bromo-4-oxospiro[3H-1,3-benzoxazine-2,4'-piperidine]-1'-carboxylate;tert-Butyl 6-BROMO-4-OXO-3,4-DIHYDRO-1'H-SPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE;TERT-BUTYL 6-BROMO-4-OXO-3,4-DIHYDROSPIRO[1,3-BENZOXAZINE-2,4'-PIPERIDINE]-1'-CARBOXYLATE;6-Bromospiro[1,3-benzoxazine-2,4'-piperidine]-4(3H)-one, N-BOC protected;SCHEMBL551786;DTXSID80383388;FKBBJWUNJKLMBK-UHFFFAOYSA-N;MFCD05865135;AKOS022175850;MS-22221;CS-0362705;FT-0710678;D78720;6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester;spiro[2h-1,3-benzoxazine-2,4'-piperidine]-1'-carboxylic acid, 6-bromo-3,4-dihydro-4-oxo-, 1,1-dimethylethyl ester;Spiro[2h-1,3-benzoxazine-2,4'-piperidine]-1'-carboxylicacid,6-bromo-3,4-dihydro-4-oxo-,1,1-dimethylethyl ester;tert-Butyl6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate

Chemical Property of tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate

Chemical Property:

• Melting Point: 226 °C
• Boiling Point: 571.5 °C at 760 mmHg
• Flash Point: 299.4 °C
• Density: 1.49 g/cm³
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 396.06847
• Heavy Atom Count: 24
• Complexity: 511

Purity/Quality:

98%min ^*data from raw suppliers

6-Bromospiro[1,3-benzoxazine-2,4'-piperidine]-4(3H)-one, N-Boc protected 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2(CC1)NC(=O)C3=C(O2)C=CC(=C3)Br

Technology Process of tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate

There total 1 articles about tert-Butyl 6-bromo-4-oxo-3,4-dihydrospiro[benzo[e][1,3]oxazine-2,4'-piperidine]-1'-carboxylate 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: 63.0%

5-bromo-2-hydroxybenzamide (6329-74-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester (690632-05-4)

Guidance literature:

With pyrrolidine; at 72 ℃; for 2h; Microwave irradiation;

DOI:10.1016/j.ejmech.2013.03.061

Reference yield:

6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester (690632-05-4) → C24H26N2O4 (1192129-07-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / Inert atmosphere

2.2: 3 h / 80 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C

4.1: potassium carbonate; sodium tris(acetoxy)borohydride / dichloromethane; water / 3 h / 20 °C

With hydrogenchloride; palladium diacetate; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 1.1: |Heck Reaction;

DOI:10.1016/j.ejmech.2013.03.061

Reference yield:

6-bromo-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-1'-carboxylic acid tert-butyl ester (690632-05-4) → C23H24N2O4*ClH (1192129-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 9 h / 100 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / Inert atmosphere

2.2: 3 h / 80 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane / 4 h / 20 °C

4.1: potassium carbonate; sodium tris(acetoxy)borohydride / dichloromethane; water / 3 h / 20 °C

5.1: hydrogenchloride / water; acetic acid / 4 h / 85 °C

With hydrogenchloride; palladium diacetate; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine; In 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; mineral oil; 1.1: |Heck Reaction;

DOI:10.1016/j.ejmech.2013.03.061

upstream raw materials:

5-bromo-2-hydroxybenzamide

N-tert-butyloxycarbonylpiperidin-4-one

Downstream raw materials:

C₂₄H₂₆N₂O₄

(E)-3-{1'-benzyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,4'-piperidin]-6-yl}-acrylic acid

C₂₂H₂₁FN₂O₄

C₂₃H₂₄N₂O₄

Refernces

• 1、 -. "Spirocyclic derivatives as histone deacetylase inhibitors". Page/Page column 31-32. . Retrieved 2009/11/30.