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

HRID 2053707Notes

Reaction equation

HRID 2053707 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=3)[CH2:12][C@H:11]2[OH:22])=[O:8])=[CH:3][CH:2]=1.[H][H]>[Pd].CN(C=O)C>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:2]=[CH:3][C:4]([C:7]([NH:9][C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[CH2:12][C@H:11]2[OH:22])=[O:8])=[CH:5][CH:6]=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-aminoindane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-nitroindane 55.7 g, 550 mL of DMF and 2.8 g of 10% Pd/C catalyst. Hydrogenate at 50 psi (345 kPa) of hydrogen at ambient temperature for 4.75 h. Filter the reaction mixture and dilute the filtrate with 1200 mL of water to give a slurry. Stir the slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. Combine the dried product and about 1 L of water and slurry for 30 minutes, filter, wash with water, and dry in vacuo at 50° C. to afford 45.4 g (90%) of 1 (R)-(4-biphenylcarbonylamino)-2(R)-hydroxy-6-aminoindane: 1R (KBr, cm−1); 3584, 3364, 3277, 1632, 1543, 1326, 1073, 743; HRMS calc'd for C22H20N2O2: 344,4120; Found: 344,1525.

Workup

  1. filtrationFilter the reaction mixture
  2. additiondilute the filtrate with 1200 mL of water
  3. customto give a slurry
  4. filtrationfilter
  5. washwash with water
  6. customdry in vacuo at 50° C
  7. customfor 30 minutes
  8. filtrationfilter
  9. washwash with water
  10. customdry in vacuo at 50° C.

Sources & evidence

ORD record
ord-fe0b71b0a9724c8889e40d0945bc2e7a
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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