4-{[(1R,3S,4S)-3-([tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy)methyl)cyclopentyl]oxy}-3-nitropyridin-2-amine → 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}pyridine-2,3-diamine

HRID 1677998Notes

Reaction equation

HRID 1677998 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@@H:11]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[C:25]=2[N+:31]([O-])=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(=O)C.[Zn]>[Si:1]([O:8][C@@H:9]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:12][C@@H:11]([O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[C:25]=2[NH2:31])[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 667981204-{[(1R,3S,4S)-3-([tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy)methyl)cyclopentyl]oxy}-3-nitropyridin-2-amine

Product 1

HCID 667979604-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}pyridine-2,3-diamineYield 88%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-3-nitropyridin-2-amine (0.361 g, 0.000725 mol) in CH2Cl2 (6.00 mL) and acetic acid (3.00 mL) was added zinc (0.474 g, 0.00725 mol) and the mixture was stirred for 30 min. The suspension was filtered and the filtrate was concentrated. The residue was dissolved in 50 ml EtOAc and 3 ml Et3N then washed with water (2×10 mL). The organic layer was dried (MgSO4) and concentrated to afford the crude product (0.297 g, 88%).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 50 ml EtOAc
  4. wash3 ml Et3N then washed with water (2×10 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94c6c466e0fe431f86bce9ff128c5ba4
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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