Trifluoroacetic acid → HCID 86615091, compound

HRID 1728031Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:33])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH2:26]Cl)[CH:11]3[C:28]([CH2:31][CH3:32])=[CH:29][CH3:30])[C:5]2=[CH:4][CH:3]=1.[CH3:34]OC([Si](C)(C)C)C.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1.FC(F)(F)C(O)=O>>[CH:13]([N:12]([CH2:24][CH3:25])[CH:11]([CH3:10])[CH3:28])([CH3:14])[CH3:34].[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:33])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH2:26][N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[CH:11]3[C:28]([CH2:31][CH3:32])=[CH:29][CH3:30])[C:5]2=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 8083Morpholine

HCID 775800946-Chloro-4'-(3-chloro-phenyl)-1'-(3-chloro-propyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Product 2

HCID 81531Diisopropylethylamine

HCID 86615091HCID 86615091, compoundYield 57%

Procedure

In a manner similar to the method described in example 60b, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-1′-(3-chloro-propyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane prepared in example 83a (0.3 g, 0.47 mmol) was reacted with morpholine (12 mL), trifluoroacetic acid (5 mL) and then N,N-diisopropylethylamine (2 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-propenyl)-1′-(3-morpholin-4-yl-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (0.15 g, 57%).

Sources & evidence

ORD record: ord-d82123aea9ea46d389089edc7c3d8e65
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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