Benzyl 4-[6-(2,3-Dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate → 3-[6-(4-Aminobutyl)naphthalen-2-yloxy]propane-1,2-diol

HRID 1644225Notes

Reaction equation

HRID 1644225 reaction equation
[OH:1][CH:2]([CH2:30][OH:31])[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]#[C:16][CH2:17][CH2:18][NH:19]C(=O)OCC1C=CC=CC=1)[CH:9]=[CH:8]2>CO.[Pd]>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:30][OH:31])[CH:14]=[CH:13]2

Participants

4

Reactant 1

HCID 57828252Benzyl 4-[6-(2,3-Dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate

Product 1

HCID 578282353-[6-(4-Aminobutyl)naphthalen-2-yloxy]propane-1,2-diolYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of benzyl 4-[6-(2,3-dihydroxypropoxy)naphthalen-2-yl]but-3-ynylcarbamate (31, 236 mg, 0.5 mmole) and 10% Pd/C (96 mg) in MeOH (70 mL) was subjected to hydrogenation conditions (1 atm) for 1 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 32 (123 mg, 78%) as a white solid: 1H NMR (300 MHz, CD3OD) δ 7.67 (d, J=8.4 Hz, 2H), 7.56 (s, 1H), 7.30 (dd, J=8.4, 1.5 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 7.14 (dd, J=8.7, 2.4 Hz, 1H), 4.18-3.99 (m, 3H), 3.76-3.65 (m, 2H), 2.75 (dt, J=10.8, 7.2 Hz, 4H), 1.80-1.70 (m, 2H), 1.62-1.52 (m, 2H).

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-fd05cc3f2fa24631863576ffac6998cb
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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