HCID 59464179, compound → HCID 59464286, compound

HRID 1713836Notes

Reaction equation

HRID 1713836 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)[CH3:5]>CO.[Pd]>[CH3:1][O:2][CH2:3][C@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[NH2:13])[CH3:5]

Participants

4

Reactant 1

HCID 59464179HCID 59464179, compound

Product 1

HCID 59464286HCID 59464286, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-{[(1R)-2-methoxy-1-methylethyl]oxy}-3-nitrobenzene (1.00 g; 4.74 mmol) was dissolved in MeOH (20 ml) and treated with 10% palladium on carbon then placed under an atmosphere of hydrogen and stirred for 24 h. The reaction mixture was filtered then concentrated by evaporation to give the title compound (Intermediate 81) (0.88 g) as an oil; 1H NMR δ 1.18 (d, 3H), 3.24 (s, 3H), 3.34-3.42 (m, 1H), 3.42-3.52 (m, 1H), 4.37-4.49 (m, 1H), 4.90 (s, 2H), 6.04-6.11 (m, 1H), 6.10-6.18 (m, 2H), 6.83-6.91 (m, 1H); MH+ 182.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthen concentrated by evaporation

Sources & evidence

ORD record
ord-ad203ecbe76a443388849e45bfe59797
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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