HCID 57828215, compound → HCID 57828254, compound

HRID 1644219Notes

Reaction equation

HRID 1644219 reaction equation
[OH:1][CH:2]([CH2:30][OH:31])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19]C(=O)OCC2C=CC=CC=2)=[CH:7][CH:6]=1>CO.[Pd]>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:30][OH:31])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57828215HCID 57828215, compound

Product 1

HCID 57828254HCID 57828254, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 4-[4-(2,3-dihydroxypropoxy)naphthalen-1-yl]butylcarbamate (22, 340 mg, 0.80 mmole) and 10% Pd/C (50 mg) in MeOH (50 mL) was subjected to hydrogenation conditions (1 atm) for 2 h at room temperature. The reaction mixture was filtered through a plug of diatomaceous earth and the plug was washed with MeOH. The filtrate was then concentrated in vacuo to afford diol 23 (226 mg, 97%) as a yellow solid: MS m/z 290 [C17H23NO3+H]+. Diol 23 was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  2. washthe plug was washed with MeOH
  3. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-05c2c43d5442411d8508cc40d9dd5028
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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