(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane → (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane

HRID 2053705Notes

Reaction equation

HRID 2053705 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C@@H:9]([OH:28])[C@@H:10]2[NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[O:15])=[CH:6][CH:5]=1)([O-])=O.[H][H]>CN(C=O)C.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C@@H:9]([OH:28])[C@@H:10]2[NH:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 44185808(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindaneHCID 178418361HCID 178418361, compound

Product 1

HCID 44185809(R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindaneYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine a slurry of 0.176 kg of 10% Pd-C (50% water wet) and 1.7 kg of biphenyl-4-carboxylic acid (R)-(6-nitro-2(R)-hydroxyindan-1-yl)amide in 17.5 L of DMF with hydrogen (50 psi, 345 kPa). After 19 h, filter the reaction mixture, add a portion of the DMF solution (5 L) to water (10 L), and stir the slurry for 2 h-repeat twice to work up the entire reaction volume. Filter the slurries together, and wash the resulting filter cake with water (3×7 L). Dry the filter cake to afford 1.42 kg of biphenyl-4-carboxylic acid (R)-(6-amino-2(R)-hydroxyindan-1-yl)amide.

Workup

  1. filtrationfilter the reaction mixture
  2. additionadd a portion of the DMF solution (5 L) to water (10 L)
  3. filtrationFilter the slurries together
  4. washwash the resulting
  5. filtrationfilter cake with water (3×7 L)
  6. customDry the filter cake

Sources & evidence

ORD record
ord-92c727de71b746edb61e244cda818397
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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