HCID 86687109, compound → HCID 89623862, compound

HRID 2285095Notes

Reaction equation

HRID 2285095 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])C1C=CC=CC=1>[Pd]>[C:21]([O:20][C:18]([CH2:17][CH2:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 1

HCID 86687109HCID 86687109, compound

Product 1

HCID 89623862HCID 89623862, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of Intermediate 84a (1.10 g, 3.29 mmol) in IMS (25.0 mL) was added to palladium on charcoal (10 wt %, 110 mg) and the reaction stirred under H2 for 1 h. The mixture was filtered through Celite and evaporated in vacuo to give the title compound (840 mg, 99%). 1H NMR (300 MHz, d4-MeOD): 1.48 (9H, s), 1.91 (1H, m), 2.02-2.24 (2H, m), 2.41 (1H, m), 2.74 (2H, t, J 7.1), 3.13 (1H, ddd, J 11.1, 10.2, 7.0), 3.32-3.53 (2H, m), 3.72 (1H, ddd, J 11.0, 7.2, 3.5), 3.89 (1H, dd, J 9.5, 5.3).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-a983bf236fb24fefb9948909df79700c
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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