HCID 69287441, compound → HCID 69286503, compound

HRID 2250319Notes

Reaction equation

HRID 2250319 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:13][CH2:12]1)C1C=CC=CC=1>[Pd].CO>[NH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][OH:8])[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 69287441HCID 69287441, compound

Product 1

HCID 69286503HCID 69286503, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5a (0.3 g, 1.03 mmol) and catalyst (10% palladium on carbon, 0.8 g, 50% wet) in methanol (25 mL) was placed in a Parr shaker bottle. The system was vacuumed and flushed with nitrogen. The procedure was repeated three times. The mixture was then shaken at room temperature overnight under 40 psi hydrogen atmosphere. The system was then vacuumed again and flushed with nitrogen. The procedure was repeated three times. The catalyst was filtered under vacuum and washed with methanol (2×10 mL). The filtrate and washings were combined and concentrated under reduced pressure to provide 6a (186 mg, 90%). The crude product was used directly without purification. m/z (ESI): 201 [C11H24N2O+H]+.

Workup

  1. customflushed with nitrogen
  2. customflushed with nitrogen
  3. filtrationThe catalyst was filtered under vacuum
  4. washwashed with methanol (2×10 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd55de02949e4e0288009a34f2f6c6f5
Source dataset
uspto-grants-2008_01
Patent number
US07317013B2

Reaction notes

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