Ammonium Chloride → 1-(3-((tert-Butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)ethanone

HRID 2203665Notes

Reaction equation

HRID 2203665 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25](N(OC)C)=[O:26])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25](=[O:26])[CH3:31])[CH2:20]1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 123599473HCID 123599473, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 1189941801-(3-((tert-Butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)ethanoneYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 3-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N-methylbicyclo[3.1.0]hexane-6-carboxamide (37 g, 87 mmol) in anhydrous tetrahydrofuran (500 mL) was added dropwise methylmagnesium bromide (87 mL, 262 mmol, 3.0 M in diethyl ether). After 3 h, saturated aqueous ammonium chloride was added to the reaction mixture. The resulting aqueous solution was extracted with ethyl acetate (3×100 mL). The combined organics were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated to yield crude 1-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)ethanone as a light brown solid (30.0 g, 91%) which was used without further purification.

Workup

  1. extractionThe resulting aqueous solution was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organics were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61dae779ec01466e9e9e0e7f1383d01a
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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