Ammonium Acetate → (5-Amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

HRID 1696873Notes

Reaction equation

HRID 1696873 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C:14](=O)[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:27])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 59192613HCID 59192613, compound

Product 1

HCID 59192558(5-Amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (10.0 g, 36.2 mmol) in methanol (300 mL) was added ammonium acetate (55.0 g, 714 mmol) at room temperature under nitrogen. After being stirred for 4 hours at room temperature, the reaction mixture was cooled to 0° C. and sodium cyanoborohydride (5.7 g, 90 mmol) was added. The resulting mixture was allowed to warm to room temperature and stirred for an additional 48 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added saturated sodium carbonate solution to adjust the pH to about 7, and the resulting solution was extracted with ethyl acetate (500 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Column chromatography (silica gel, 100-200 mesh, 2% to 5% methanol in dichloromethane) gave (5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (4.6 g, 46%) as a solid. MS cald. for C16H23NO3 277. obsd. 278 [(M+H)+].

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for an additional 48 hours
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. additionTo the residue was added saturated sodium carbonate solution
  6. extractionthe resulting solution was extracted with ethyl acetate (500 mL×3)
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f75b602544f42c0a667d9ad9a694390
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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