Ethanol → 1-(5-amino-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yloxy)phenyl)-4-methyl-1H-tetrazol-5(4H)-one

HRID 1754446Notes

Reaction equation

HRID 1754446 reaction equation
[Si:1]([O:8][CH2:9][C:10]([CH3:29])([O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[N:22]1[C:26](=[O:27])[N:25]([CH3:28])[N:24]=[N:23]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCO.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>O.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]([CH3:29])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:14]([N:22]2[C:26](=[O:27])[N:25]([CH3:28])[N:24]=[N:23]2)[CH:15]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 493570RiboflavinHCID 867044871-(2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yloxy)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one

Product 1

HCID 867044881-(5-amino-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yloxy)phenyl)-4-methyl-1H-tetrazol-5(4H)-oneYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A round-bottom flask was charged with 1-(2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yloxy)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one (2.54 g, 6.00 mmol), EtOH (60 mL), and 10% Pd/C (50% in water, Degussa type E101; 510 mg, 20 wt % by weight of the starting nitro compound). The flask was sealed with a rubber septum, degassed, and back-filled with H2 (3×) from a balloon filled with H2. The reaction was stirred for 4 h using a H2 filled balloon. The reaction mixture was filtered through a pad of celite, and the pad of celite was rinsed with EtOAc/MeOH. The filtrate was evaporated to dryness to provide 1-(5-amino-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yloxy)phenyl)-4-methyl-1H-tetrazol-5(4H)-one (2.26 g, 96%) as a light brown solid that was used without further purification.

Workup

  1. customThe flask was sealed with a rubber septum
  2. customdegassed
  3. additionback-filled with H2 (3×) from a balloon
  4. additionfilled with H2
  5. filtrationThe reaction mixture was filtered through a pad of celite
  6. washthe pad of celite was rinsed with EtOAc/MeOH
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c37d40a9af634883af602b04cba8e897
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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