HCID 118022913, compound → HCID 118022741, compound

HRID 522671Notes

Reaction equation

HRID 522671 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C:5]([CH3:8])([CH3:7])[C@@H:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[O:3]1>CCOC(C)=O.CC(O)C.[Pd]>[CH3:1][C:2]1([CH3:18])[O:3][C@H:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[C:5]([CH3:8])([CH3:7])[O:6]1

Participants

4

Reactant 1

HCID 118022913HCID 118022913, compound

Product 1

HCID 118022741HCID 118022741, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22055037Isopropanol ethyl acetateSolvent

Procedure

A mixture of (R)-2,2,4,4-tetramethyl-5-(4-nitrophenyl)-1,3-dioxolane (200 mg, 0.797 mmol) and Pd/C (10%, 60 mg) in EtOAc/IPA (10 mL/10 mL) was stirred under 1 atm H2 atmosphere (balloon) at RT for 16 h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford the desired product (180 mg, 100%), which was directly used into the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-efe44a5bfd0542979b0069785846bce7
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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