HCID 86634822, compound → HCID 68785405, compound

HRID 1808136Notes

Reaction equation

HRID 1808136 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:18]C(=O)OCC2C=CC=CC=2)[C:12]2[O:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:2]1>O1CCCC1.[Pd]>[NH2:18][C@H:11]([C:12]1[O:13][C:14](=[O:17])[NH:15][N:16]=1)[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 1

HCID 86634822HCID 86634822, compound

Product 1

HCID 68785405HCID 68785405, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-benzyl 2-(1H-indol-3-yl)-1-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl-carbamate (1.41 g, 3.73 mmol) in anhydrous tetrahydrofuran (100 mL) was mixed with 10% palladium on activated carbon (160 mg) and hydrogenated for 24 h at room temperature and at 3 bar. A further portion of 20% palladium on activated carbon (160 mg) was added and the mixture hydrogenated for a further 24 h at 3 bar and 40° C. The catalyst was then filtered off, the filtrate concentrated to low volume in a vacuum and the residue (1.24 g) purified by flash chromatography (100 g, 20×4.0 cm) with chloroform/methanol (95:5).

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate concentrated to low volume in a vacuum
  3. customthe residue (1.24 g) purified by flash chromatography (100 g, 20×4.0 cm) with chloroform/methanol (95:5)

Sources & evidence

ORD record
ord-ef8addb7109c461f9d08c58966fd11a7
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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