(R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine → (R)-3-Methoxy-4-(3-triisopropylsilanyloxy-pyrrolidin-1-yl)-phenylamine

HRID 601514Notes

Reaction equation

HRID 601514 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:16][CH2:15][C@@H:14]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH2:13]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:16][CH2:15][C@@H:14]([O:17][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:21])[CH3:20])[CH2:13]1

Participants

4

Reactant 1

HCID 57870244(R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine

Product 1

HCID 57870268(R)-3-Methoxy-4-(3-triisopropylsilanyloxy-pyrrolidin-1-yl)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve (R)-1-(2-Methoxy-4-nitro-phenyl)-3-triisopropylsilanyloxy-pyrrolidine (12 g, 30.4 mmol) in EtOH (200 mL) and add 5% Pd/C (1.26 g). Purge the black mixture with hydrogen (1 atm) and stir overnight under a hydrogen atmosphere at ambient temperature at 60 psi. Filter the black mixture through Celite® and wash the solids with additional EtOH (100 mL). Concentrate the filtrate to give the title compound as a dark brown oil. 1H NMR (400 MHz, CDCl3): δ 6.76 (d, 1H, J=8.8 Hz), 6.31 (d, 1H, J=2.6 Hz), 6.25 (dd, 1H, J=8.8, 2.6 Hz), 3.74 (s, 3H), 1.34 (s, 9H). Note: title compound decomposed rapidly. Store compound in freezer immediately after use. MS (ES+) 365.2 (M+1)+.

Workup

  1. customPurge the black mixture with hydrogen (1 atm)
  2. filtrationFilter the black mixture through Celite®
  3. washwash the solids with additional EtOH (100 mL)
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-4674d0f267a04d64b42c55a434ec2aee
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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