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 → racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2,3-dihydroxy-propyl)-2'-(1-methylcyclopropyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728216Notes

Reaction equation

HRID 1728216 reaction equation
[Br: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][CH:25]([OH:28])[CH2:26][OH:27])[CH:11]3[C:29]3([CH3:32])[CH2:31][CH2:30]3)[C:5]2=[CH:4][CH:3]=1.COC([Si](C)(C)C)C>FC(F)(F)C(O)=O>[Br: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][CH:25]([OH:28])[CH2:26][OH:27])[CH:11]3[C:29]3([CH3:32])[CH2:31][CH2:30]3)[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 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 trimethylsilane

Product 1

HCID 76568027racemic (2'R,3R,4'S)-6-bromo-4'-(3-chlorophenyl)-1'-(2,3-dihydroxy-propyl)-2'-(1-methylcyclopropyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 63%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The compound 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 (40 mg, 0.06 mmol) was dissolved in trifluoroacetic acid (3 mL). The solution was stirred at room temperature for 1 h, then concentrated. The residue was dissolved in a solution of methanol (3 mL) and N,N′-diisopropylethylamine (1 mL). The reaction tube was then placed into the cavity of a focused monomode microwave reactor and the contents of the flask were irradiated at 120° C. for 30 min. The reaction mixture was concentrated and the residue was purified by Prep-HPLC to give title compound (20 mg, 63%) m/z (M+H)+: 533

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in a solution of methanol (3 mL) and N,N′-diisopropylethylamine (1 mL)
  3. customThe reaction tube was then placed into the cavity of a focused monomode microwave reactor
  4. customthe contents of the flask were irradiated at 120° C. for 30 min
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-8d75bc7cc84f4caba8a820442d659573
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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