HCID 67008226, compound → HCID 67007814, compound

HRID 1672425Notes

Reaction equation

HRID 1672425 reaction equation
C([N:8]1[CH2:20][CH2:19][C:11]2([O:16][C@H:15]([CH3:17])[CH2:14][C@@H:13]([CH3:18])[O:12]2)[C@H:10]([CH3:21])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[CH3:17][C@@H:15]1[CH2:14][C@@H:13]([CH3:18])[O:12][C:11]2([CH2:19][CH2:20][NH:8][CH2:9][C@H:10]2[CH3:21])[O:16]1

Participants

5

Reactant 2

HCID 67008226HCID 67008226, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67007814HCID 67007814, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,4R,7R)-9-benzyl-2,4,7-trimethyl-1,5-dioxa-9-azaspiro[5.5]undecane (880 mg, 3.04 mmol) from Example 2B in methanol (25 mL) was added palladium hydroxide (82 mg) and the mixture stirred under 1 atmosphere pressure of hydrogen. After 5 h, the mixture was filtered and concentrated to provide 567 mg (94%) of the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ 4.11-3.97 (m, 2H), 2.93-2.71 (m, 3H), 2.61 (dd, 1H, J=12.3, 8.7 Hz), 1.97 (ddd, 1H, J=13.9, 5.6, 3.6 Hz), 1.79-1.70 (m, 1H), 1.65-1.47 (m, 4H), 1.21 (d, 3H, J=6.4 Hz), 1.19 (d, 3H, J=6.4 Hz), 0.95 (d, 3H, J=6.7 Hz); MS (DCI/NH3) m/e 200 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f73fe3aecd3243c9870defc12d7d55e3
Source dataset
uspto-grants-2011_08
Patent number
US07998982B2

Reaction notes

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