4-(9-Azidononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman → 4-(9-Aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792310Notes

Reaction equation

HRID 1792310 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[O:16][CH2:15][C:14]1([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=1)[CH3:27])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=2)[O:16][CH2:15][C:14]1([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:32][CH:33]=1)[CH3:27]

Participants

4

Reactant 1

HCID 220331844-(9-Azidononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 220332874-(9-Aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(9-azidononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (411 mg, 0.80 mmol) in methanol (100 ml) was added 10% Pd—C (100 mg), which was then stirred overnight at room temperature under hydrogen (atmospheric pressure). The resulting mixture was filtered through cellite and concentrated under reduced pressure to give the title compound (391 mg, stoichiometric yield) as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered through cellite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3767a57b129b4c1b8e3765f731eeb162
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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