HCID 57828221, compound → Benzyl 4-[6-(tert-butyldimethylsilyloxy)naphthalen-2-yl]butan-1-amine

HRID 1644235Notes

Reaction equation

HRID 1644235 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]#[C:20][CH2:21][CH2:22][NH:23]C(=O)OCC1C=CC=CC=1)[CH:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[CH2:12]([CH:22]([NH2:23])[CH2:21][CH2:20][CH2:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2])[CH:10]=2)[CH:15]=1)[C:11]1[CH:16]=[CH:17][CH:18]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 57828221HCID 57828221, compound

Product 1

HCID 66774339Benzyl 4-[6-(tert-butyldimethylsilyloxy)naphthalen-2-yl]butan-1-amineYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 83 (8.0 g, 17.41 mmol) and 10% Pd/C (3.6 g) in MeOH (240 mL) was subjected to hydrogenation conditions (1 atm) for 6 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 concentrated in vacuo and the residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH) to afford amine 95 (3.2 g, 56%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 7.64 (d, J=6.3 Hz, 1H), 7.60 (s, 1H), 7.55 (s, 1H), 7.30 (d, J=1.5 Hz, 1H), 7.15 (s, 1H), 7.03 (dd, J=8.9 Hz, 2.3 Hz, 1H), 2.76 (t, J=7.4 Hz, 2H), 2.70 (t, J=7.2 Hz, 2H), 1.79-1.69 (m, 2H), 1.59-1.49 (m, 2H), 1.04 (s, 9H), 0.25 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of diatomaceous earth
  2. washthe plug was washed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (silica gel, 90:9:1 CHCl3/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-d73ca63ef42d471b9557f37ec76a6d09
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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