HCID 86610075, compound → HCID 45078983, compound

HRID 723862Notes

Reaction equation

HRID 723862 reaction equation
C(OC([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17](C(OCC1C=CC=CC=1)=O)[C@H:16]([CH3:31])[CH2:15]2)=O)C1C=CC=CC=1.[H][H]>C1COCC1.CO.[Pd]>[CH3:31][C@@H:16]1[CH2:15][C:14]2[C:18](=[CH:19][CH:20]=[C:12]([NH2:11])[CH:13]=2)[NH:17]1

Participants

5

Reactant 2

HCID 86610075HCID 86610075, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 45078983HCID 45078983, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of benzyl (2R)-5-{[(benzyloxy)carbonyl]amino}-2-methyl-2,3-dihydro-1H-indole-1-carboxylate (PCT/US00/08224; WO00/73301, 3.36 g, 8.07 mmol) and 10% palladium-on-carbon (108 mg) in THF/MeOH (1:1, 60 mL) is shaken on a Parr apparatus under a 36 psi hydrogen atmosphere overnight. The catalyst is removed by filtration through a pad of Celite, and the filtrate is concentrated under reduced pressure. Purification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (1–2% MeOH/CH2Cl2) affords the title compound, MS (ESI+) for C9H12N2 m/z 149 (M+H)+.

Workup

  1. customThe catalyst is removed by filtration through a pad of Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customPurification by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (1–2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fb4a4e80d4e9405e88a7d6aa86d21f4d
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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