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

Base Information

• Chemical Name: tert-Butyl 6-fluoro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate
• CAS No.: 345938-08-1
• Molecular Formula: C₁₇H₂₁FN₂O₄
• Molecular Weight: 336.363
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90519232
• Wikidata: Q72479716
• Mol file: 345938-08-1.mol

Synonyms:345938-08-1;tert-Butyl 6-fluoro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate;1'-BOC-6-FLUORO-1,2-DIHYDRO-2-OXOSPIRO[4H-3,1-BENZOXAZINE-4,4'-PIPERIDINE];tert-butyl 6-fluoro-2-oxospiro[1H-3,1-benzoxazine-4,4'-piperidine]-1'-carboxylate;tert-Butyl 6-fluoro-2-oxo-spiro[1H-3,1-benzoxazine-4,4'-piperidine]-1'-carboxylate;SCHEMBL5003859;SCHEMBL5008883;DTXSID90519232;AKOS022175271;CS-0362706;1-Boc-6-fluoro-1,2-dihydro-2-oxospiro[4H-3,1-benzoxazine-4,4-piperidine];tert-butyl 6-fluoro-2-oxo-1,2-dihydro-1'h-spiro[3,1-benzoxazine-4,4'-piperidine]-1'-carboxylate;tert-Butyl6-fluoro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate

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

Chemical Property:

• Boiling Point: 414oC at 760 mmHg
• Flash Point: 204.2oC
• PSA: 67.87000
• Density: 1.30
• LogP: 3.68990
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 336.14853532
• Heavy Atom Count: 24
• Complexity: 511

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl6-fluoro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 4 articles about tert-Butyl 6-fluoro-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-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: 95.0%

N-(tert-butoxycarbonyl)-4-fluoroaniline (60144-53-8) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4’-(tert-butoxycarbonyl)-6-fluoro-spiro[4H-3,1-benzoxazine-4,4’-piperidin]-2(1H)-one (345938-08-1)

Guidance literature:

N-(tert-butoxycarbonyl)-4-fluoroaniline; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - -15 ℃; for 4.5h; Inert atmosphere;

With lanthanium (III) chloride bis(lithium chloride) complex; In tetrahydrofuran; pentane; at -78 ℃; for 0.416667h; Inert atmosphere;

N-tert-butyloxycarbonylpiperidin-4-one; With potassium tert-butylate; In tetrahydrofuran; pentane; at -78 - 70 ℃; for 13h; Inert atmosphere;

DOI:10.1021/ml400528y

Reference yield: 42.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4’-(tert-butoxycarbonyl)-6-fluoro-spiro[4H-3,1-benzoxazine-4,4’-piperidin]-2(1H)-one (345938-08-1)

Guidance literature:

N-(tert-butoxycarbonyl)-4-fluoroaniline; With tert.-butyl lithium; In tetrahydrofuran; at -78 - -25 ℃; for 2.5h;

N-tert-butyloxycarbonylpiperidin-4-one; In tetrahydrofuran; at -78 ℃; for 4h;

With potassium tert-butylate; In tetrahydrofuran; at -78 - 20 ℃; for 18h;

Reference yield:

2-(3,4-dichloro-phenyl)-4-oxo-butyric acid methyl ester (1036926-74-5) + N-(tert-butoxycarbonyl)-4-fluoroaniline (60144-53-8) → 4’-(tert-butoxycarbonyl)-6-fluoro-spiro[4H-3,1-benzoxazine-4,4’-piperidin]-2(1H)-one (345938-08-1)

Guidance literature:

N-(tert-butoxycarbonyl)-4-fluoroaniline; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - -20 ℃; for 3.33333h;

2-(3,4-dichloro-phenyl)-4-oxo-butyric acid methyl ester; With potassium tert-butylate; In tetrahydrofuran; hexane; at -60 - 20 ℃; for 14h;

upstream raw materials:

N-tert-butyloxycarbonylpiperidin-4-one

2-(3,4-dichloro-phenyl)-4-oxo-butyric acid methyl ester

N-(tert-butoxycarbonyl)-4-fluoroaniline

di-tert-butyl dicarbonate

Downstream raw materials:

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

2-((S)-2-((S)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylbutanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-5-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-N-methylpentanamido)-3-phenylpropanamido)ethylcarbamic acid benzyl ester

2-((S)-2-((R)-2-(3,4-dichlorophenyl)-4-(6-fluoro-1-methyl-2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4'-piperidine]-1'-yl)-2-methyl butanamido)-3-phenylpropanamido)ethyl carbamic acid benzyl ester

Refernces

• 1、 -. "SPIROPIPERIDINE DERIVATIVES AS NK3 ANTAGONISTS". Page/Page column 42. . Retrieved 2008/12/07.