Toluene → HCID 57750214, compound

HRID 504514Notes

Reaction equation

HRID 504514 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:43])[C@@:10]3([C@@H:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:33])([CH3:32])[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=O)[CH2:14][C:13](=[O:34])[NH:12][C@H:11]3[C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[CH3:42])[C:5]2=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:43])[C@@:10]3([C@@H:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:33])([CH3:32])[CH2:25][NH:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH2:14][C:13](=[O:34])[NH:12][C@H:11]3[C:35]3[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=3[CH3:42])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 59428086HCID 59428086, compound

Product 1

HCID 57750214HCID 57750214, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a solution of chiral (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-methanesulfonylamino-1,1-dimethyl-2-oxo-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (20 mg, 0.03 mmol) prepared in Example 12b in THF (1 mL) was added a toluene solution (1 M) of DIBALH (0.18 mL, 0.18 mmol) in one portion. After stirred for 0.5 h, the mixture was quenched with water. Then the mixture was filtered and the filtrate was concentrated. The residue was purified by Prep-HPLC to give the title compound as a white solid (9 mg).

Workup

  1. customthe mixture was quenched with water
  2. filtrationThen the mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-73ff316163d8483ea2c9e0ecacb03928
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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