HCID 67007910, compound → HCID 67008132, compound

HRID 1672424Notes

Reaction equation

HRID 1672424 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 67007910HCID 67007910, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67008132HCID 67008132, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S,4S,7R)-9-benzyl-2,4,7-trimethyl-1,5-dioxa-9-azaspiro[5.5]undecane from Example 1A (20.30 g, 70.20 mmol) in methanol (300 mL) was added palladium hydroxide (0.986 g, 7.02 mmol) and the mixture stirred under 60 psi pressure of hydrogen. After 4 hours, the mixture was filtered and concentrated to provide 13.71 g (98%) of the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ 4.06-3.97 (m, 2H), 2.94 (dd, 1H, J=12.7, 4.0 Hz), 2.87 (dd, 2H, J=5.2, 5.2 Hz), 2.66 (dd, 1H, J=12.7, 5.6 Hz), 1.92-1.85 (m, 1H), 1.82-1.73 (m, 1H), 1.63-1.53 (m, 4H), 1.20 (d, 3H, J=6.4 Hz), 1.19 (d, 3H, J=6.4 Hz), 0.96 (d, 3H, J=7.1 Hz); MS (DCI/NH3) m/e 200 (M+H)+.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e98fca588fb245eca3b3572c5be4d4a6
Source dataset
uspto-grants-2011_08
Patent number
US07998982B2

Reaction notes

Loading…