HCID 54275101, compound → HCID 54427490, compound

HRID 1734643Notes

Reaction equation

HRID 1734643 reaction equation
[C:1]([O:4][CH:5]1[CH:9]([NH:10][C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([Cl:18])=[CH:13][C:12]=2[N+:19]([O-])=O)[CH2:8][CH:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH:6]1[O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2]>C(O)(C)C.[Ni]>[C:1]([O:4][CH:5]1[CH:9]([NH:10][C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([Cl:18])=[CH:13][C:12]=2[NH2:19])[CH2:8][CH:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH:6]1[O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 54275101HCID 54275101, compound

Product 1

HCID 54427490HCID 54427490, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

(±)-(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(4,5-dichloro-2-nitroanilino)-1,2-cyclopentanediyl diacetate (4.30 g, 9.28 mmol) in isopropanol (250 mL) was shaken with Raney nickel (Aldrich, slurry in water, 400 mg wet) under hydrogen (50 psi) on a Parr shaker for 2.75 hours. Catalyst was filtered off with Celite and the filtrate-wash (350 mL) stored at -5° C. Yellow crystals of title compound formed slowly (2.35 g, 58%), m.p. 124°-125° C.; 1H-NMR(DMSO-d6)δ: 6.70 and 6.57 (both s, 1 each, 2 aromatic CH), 5.15-4.9 (m, 5, NH2, NH, and 2 OCH), 4.2-4.0 (m, 2, CH2O), 3.9-3.75 (m, 1, NCH), 2.5-2.4 (m overlapping solvent, CH2), 2.07, 2.04, and 2.01 (all s, 9, 3 CH3), 1.4-1.2 (m, 1, CH); mass spectrum(CI): 433(M+1).

Workup

  1. filtrationCatalyst was filtered off with Celite
  2. washthe filtrate-wash (350 mL)
  3. customstored at -5° C

Sources & evidence

ORD record
ord-f73a0c8744c149d4bea6f7a60eb6e399
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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