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

HRID 1644228Notes

Reaction equation

HRID 1644228 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]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 57828221HCID 57828221, compound

Product 1

HCID 578282274-[6-(tert-Butyldimethylsilyloxy)naphthalen-2-yl]butan-1-amineYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of crude 29 (900 mg) and 10% Pd/C (400 mg) in MeOH (50 mL) was subject 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, 80:18:2 CHCl3/CH3OH/NH4OH) to afford amine 77 (405 mg, 27% over two steps) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.62 (t, J=8.9, 2H), 7.52 (br s, 1H), 7.26 (dd, J=8.4, 1.7 Hz, 1H), 7.15 (d, J=2.2 Hz, 1H), 7.04 (dd, J=8.8, 2.5 Hz, 1H), 3.03-2.37 (br s, 1H), 2.74 (t, J=7.5 Hz, 2H), 1.78-1.65 (m, 2H), 1.58-1.47 (m, 2H), 1.01 (s, 9H), 0.23 (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, 80:18:2 CHCl3/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-db72fc51f07a427990e7ace8eab8653b
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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