1-(2-Nitrophenyl)-2,2-dimethyl-1-propanol → HCID 86639080, compound

HRID 333470Notes

Reaction equation

HRID 333470 reaction equation
[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10](Cl)=[O:11].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([OH:28])[C:24]([CH3:27])([CH3:26])[CH3:25])([O-:16])=[O:15]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([O:28][CH:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15])[C:24]([CH3:25])([CH3:26])[CH3:27])=[O:11]

Participants

5

Reactant 2

HCID 591895461-(2-Nitrophenyl)-2,2-dimethyl-1-propanolHCID 71432218(1s)-Camphanoyl chloride

Product 1

HCID 86639080HCID 86639080, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere, (1S)-camphanic acid chloride (3.37 g, 15.6 mmol) was added to a solution of (RS)-1-(2-nitrophenyl)-2,2-dimethyl-1-propanol (2.71 g, 13 mmol) and DMAP (80 mg, 0.65 mmol) in anhydrous pyridine (50 mL). The mixture was stirred for 24 hours at room temperature. Solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (50 mL), washed with 0.5 M HCl (20 mL) twice followed with saturated NaHCO3 solution (20 mL). The organic phase was dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to yield (RS)-1-(2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (4.11 g, 81%, 1:1 mixture of diastereomers) as a yellow solid. 1H NMR (400 MHz, CDCl3) for diastereomers: δ 7.91 (m, 1H, Ph-H), 7.62 (m, 2H, Ph-H), 7.46 (m, 1H, Ph-H), 6.66 and 6.62 (2 s, 1H, Ph-CH), 2.38 (m, 1H), 2.10-1.9 (m, 2H), 1.71 (m, 1H), 1.13, 1.11, 1.08, 1.04, 1.03, 0.87 (6 s, 9H, CH3×3), 0.97 (s, 9H, (CH3)3C).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with 0.5 M HCl (20 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-761f8f0764d749eab55e83df99fc594e
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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