8-(1-Hydroxy-1-(1-hydroxy-4-methyl-1,3-dihydroisobenzofuran-5-yl)-2-methylpropan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one → 8-(1-Hydroxy-2-methyl-1-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)propan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1848561Notes

Reaction equation

HRID 1848561 reaction equation
[OH:1][CH:2]([C:24]1[C:25]([CH3:34])=[C:26]2[C:30](=[CH:31][CH:32]=1)[CH:29]([OH:33])[O:28][CH2:27]2)[C:3]([N:6]1[CH2:23][CH2:22][C:9]2([C:13](=[O:14])[N:12]([C:15]3[CH2:16][O:17][C:18](=[O:21])[C:19]=3[CH3:20])[CH2:11][CH2:10]2)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[OH:1][CH:2]([C:24]1[C:25]([CH3:34])=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][CH2:27]2)[C:3]([N:6]1[CH2:7][CH2:8][C:9]2([C:13](=[O:14])[N:12]([C:15]3[CH2:16][O:17][C:18](=[O:21])[C:19]=3[CH3:20])[CH2:11][CH2:10]2)[CH2:22][CH2:23]1)([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 867095428-(1-Hydroxy-1-(1-hydroxy-4-methyl-1,3-dihydroisobenzofuran-5-yl)-2-methylpropan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 867095438-(1-Hydroxy-2-methyl-1-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)propan-2-yl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product of Step J (340 mg, 0.723 mmol) in methylene chloride (30 mL) was added PCC (311 mg, 1.45 mmol) at 0° C. and the resulting solution was stirred at 0° C. for 2 h. The reaction mixture was partitioned between methylene chloride and saturated bicarbonate, and the alkaline phase was extracted with methylene chloride (3×50 mL). The combined organic phase was dried over sodium sulfate, concentrated and the residue was purified on TLC using 10% methanol/methylene chloride as developing solvents to give the title compound. LC/MS: (M+1)+: 469.20.

Workup

  1. customThe reaction mixture was partitioned between methylene chloride and saturated bicarbonate
  2. extractionthe alkaline phase was extracted with methylene chloride (3×50 mL)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified on TLC

Sources & evidence

ORD record
ord-b1650cc7f6834057987c1f9b29e99911
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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