Water → HCID 11098580, compound

HRID 2217186Notes

Reaction equation

HRID 2217186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:21]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:13](=[O:21])[CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 10968084HCID 10968084, compound

Product 1

HCID 11098580HCID 11098580, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a vigorously stirred solution of RuCl3.H2O (2.39 g, 11.5 mmol) and NaIO4 (24.6 g, 115.0 mmol) in water (250 mL) was added (S)-piperidine-1,2-dicarboxylic acid di-tert-butyl ester (8.22 g, 28.8 mmol) in ethyl acetate (250 mL) at room temperature. After stirring for 4 h, the reaction mixture was partitioned and the aqueous layer washed with ethyl acetate. To the combined organic layers was added iPrOH (2.5 mL) and stirring was continued for 2 hours in order to destroy excess RuO4. The precipitate was removed by filtration through a pad of celite and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the title compound as a pale yellow oil, which crystallized upon standing (6.69 g, 78%): 1H NMR (400 MHz, CDCl3) δ 1.49 (9H, s), 1.52 (9H, s), 1.75-1.82 (2H, m), 1.97-2.06 (1H, m), 2.15-2.21 (1H, m), 2.41-2.61 (2H, m), 4.59 (1H, dd, J 3.5 Hz)

Workup

  1. customthe reaction mixture was partitioned
  2. washthe aqueous layer washed with ethyl acetate
  3. additionTo the combined organic layers was added iPrOH (2.5 mL)
  4. stirringstirring
  5. waitwas continued for 2 hours in order
  6. customto destroy excess RuO4
  7. customThe precipitate was removed by filtration through a pad of celite
  8. customthe filtrate was evaporated under reduced pressure
  9. customThe residue was purified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-55fe8fe65ccd4b51a3c69967d2a86dc4
Source dataset
uspto-grants-2008_08
Patent number
US07407964B2

Reaction notes

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