(3S,3'S,4'R,6'R,8'S,8'aR)-6-chloro-8'-(3-chloro-2-fluorophenyl)-6'-(2,2-dimethylpropyl)-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-1',2-dione synthesis

7synthesis methods

Product Name:(3S,3'S,4'R,6'R,8'S,8'aR)-6-chloro-8'-(3-chloro-2-fluorophenyl)-6'-(2,2-dimethylpropyl)-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-1',2-dione
CAS Number:897365-81-0
Molecular formula:C37H33Cl2FN2O3
Molecular Weight:643.5739

2987-16-8 Synthesis

2987-16-8
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2H-Indol-2-one, 6-chloro-3-[(3-chloro-2-fluorophenyl)Methylene]-1,3-dihydro-

897365-76-3
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282735-66-4 Synthesis

282735-66-4
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(3S,3'S,4'R,6'R,8'S,8'aR)-6-chloro-8'-(3-chloro-2-fluorophenyl)-6'-(2,2-dimethylpropyl)-3',4'-diphenylspiro[1H-indole-3,7'-4,6,8,8a-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine]-1',2-dione

897365-81-0
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Yield:897365-81-0 66%

Reaction Conditions:

in toluene at 80; for 18 h;

Steps:

8

Example 8 Preparation of chiral(2'R,3'S,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester; To a mixture of (5R,6S)-5,6-diphenylmorpholin-2-one (3.4 g, 13.4 mmol, ArkPharminc) in toluene (80 mL) was added E/Z-6-chloro-3-(3-chloro-2-fluorobenzylidene)indolin-2-one (3.5 g, 11.3 mmol) prepared in Example 2, 3,3-dimethylbutyraldehyde (1.3 g, 13.4 mmol, Aldrich). The reaction mixture was stirred at 80° C. for 18 h. The mixture was filtered through a short pad of celite. The pad was washed with additional toluene. The filtrates were combined, and concentrated. The residue was purified by chromatography (10-25% EtOAc inhexanes) to give desired 1,3-dipolar product chiral(3S,3'S,4'R,6'R,8'S,8a'R)-6-chloro-8'-(3-chloro-2-fluorophenyl)-6'-neopentyl-3',4'-diphenyl-3',4',8',8a'-tetrahydrospiro[indoline-3,7'-pyrrolo[2,1-c][1,4]oxazine]-1',2(6'H)-dione as a yellow foam (Yield, 5.7 g, 66%).

References:

US2011/269809,2011,A1 Location in patent:Page/Page column 10

85070-48-0 Synthesis