2-Cyclopentyl-4-(4-methylpent-1-ynyl)-5-nitrophenyl methyl carbonate → 5-Amino-2-cyclopentyl-4-(4-methylpent-1-ynyl)phenyl methyl carbonate

HRID 471941Notes

Reaction equation

HRID 471941 reaction equation
[C:1](=[O:25])([O:23][CH3:24])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([C:12]#[C:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)(=O)C.O.CO.[Zn]>[C:1](=[O:25])([O:23][CH3:24])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([C:12]#[C:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:5][C:4]=1[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 1

HCID 593950772-Cyclopentyl-4-(4-methylpent-1-ynyl)-5-nitrophenyl methyl carbonate

Product 1

HCID 593950535-Amino-2-cyclopentyl-4-(4-methylpent-1-ynyl)phenyl methyl carbonateYield 99%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Cyclopentyl-4-(4-methylpent-1-ynyl)-5-nitrophenyl methyl carbonate (75 mg, 0.22 mmol) was dissolved in a mixture of glacial acetic acid (940 μL) and water (235 μL). Zn dust (71 mg, 1.09 mmol) was added at room temperature and the reaction stirred for 10 min. The reaction was diluted with methanol (5 mL), filtered and concentrated. The product was brought up in dichloromethane, washed with 50% saturated NaHCO3, dried over Na2SO4, filtered, and dried down to provide 5-amino-2-cyclopentyl-4-(4-methylpent-1-ynyl)phenyl methyl carbonate as a clear orange oil (68 mg, 99% yield). LC/MS m/z 316.2 [M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. washwashed with 50% saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customdried down

Sources & evidence

ORD record
ord-eb51fd8292654d469543a722cb90fb69
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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