HCID 178458199, compound → HCID 178464710, compound

HRID 2389182Notes

Reaction equation

HRID 2389182 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:29]([F:32])([F:31])[F:30])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]([N+:26]([O-])=O)([CH3:25])[CH2:23][OH:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.CO.[Zn]>[NH2:26][C:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:7][CH2:6][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:9]3)[C:13]=2[C:29]([F:31])([F:32])[F:30])[CH:18]=1)([CH3:25])[CH2:23][OH:24]

Participants

5

Reactant 1

HCID 178458199HCID 178458199, compound

Product 1

HCID 178464710HCID 178464710, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2-[6-(trans-4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-2-nitro-propan-1-ol (57 mg, 0.00012 mol) was dissolved in acetic acid (0.50 mL, Fisher), followed by addition of zinc (76 mg, 0.0012 mol, Aldrich) dust in small portions at room temperature. The reaction mixture was then allowed to stir at room temperature for 1.5 hours. The reaction was diluted with methanol, filtered and evaporated. The white solid was taken up in methylene chloride, washed with 1N NaOH, washed with water, dried with magnesium sulfate, filtered and evaporated. 45 mg of product isolated (85%). MS: m/z=424.57 [M+H]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.20 (dd, J=9.3, 1.5 Hz, 1H), 7.90-7.95 (m, 1H), 7.89 (d, J=1.8 Hz, 1H), 7.63 (dd, J=9.2, 2.1 Hz, 1H), 7.31 (d, J=9.0 Hz, 1H), 4.24-4.34 (m, 1H), 3.77 (d, J=10.5 Hz, 1H), 3.68 (d, J=10.5 Hz, 1H), 2.14-2.23 (m, 2H), 1.94-2.13 (m, 3H), 1.81-1.92 (m, 2H), 1.48-1.59 (m, 5H), 1.24-1.38 (m, 1H), 1.03-1.19 (m, 3H), 0.88 (s, 9H).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. washwashed with 1N NaOH
  4. washwashed with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ed259ce62bfe47aeb54d3cd9a18e9fa7
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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