Acetone → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2,3-dihydroxy-propyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728215Notes

Reaction equation

HRID 1728215 reaction equation
C([N:4]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]2([C:25]3[C:20](=[CH:21][C:22]([Br:26])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:27])[CH:5]1[C:28]1([CH3:31])[CH2:30][CH2:29]1)C=C.[CH3:32][O:33][CH:34]([Si:36]([CH3:39])([CH3:38])[CH3:37])[CH3:35].C[N+]1([O-])CCOCC1.[CH3:48][C:49]([CH3:51])=[O:50]>O.O=[Os](=O)(=O)=O>[Br:26][C:22]1[CH:21]=[C:20]2[NH:19][C:18](=[O:27])[C:6]3([CH:7]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=4)[CH2:8][C:9](=[O:10])[N:4]([CH2:48][CH:49]([OH:50])[CH2:51][OH:33])[CH:5]3[C:28]3([CH3:31])[CH2:30][CH2:29]3)[C:25]2=[CH:24][CH:23]=1.[CH3:32][O:33][CH:34]([Si:36]([CH3:39])([CH3:38])[CH3:37])[CH3:35]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 77579449racemic (2'R,3R,4'S)-1'-allyl-6-bromo-4'-(3-chlorophenyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Product 1

HCID 77580230racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2,3-dihydroxy-propyl)-2'-(1-methyl cyclopropyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalyst

Procedure

To a mixture of racemic (2′R,3R,4′S)-1′-allyl-6-bromo-4′-(3-chlorophenyl)-2′-(1-methyl cyclopropyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (100 mg, 0.16 mmol), N-methylmorpholine N-oxide (30 mg, 0.22 mmol) and 3 drops of water in acetone (3 mL) was added OsO4 (10 mg, 0.04 mmol). The mixture was stirred at room temperature for 1 h, then purified by Prep-HPLC to give the title compound as a white solid (40 mg, 37%).

Workup

  1. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-8f7e1fb0169841b19452f985114f561b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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