Sodium Hydroxide → HCID 22399683, compound

HRID 1734284Notes

Reaction equation

HRID 1734284 reaction equation
[CH2:1]([CH2:8][Si:9]([C:12]([Si](CCC1C=CC=CC=1)(C)C)=O)([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#[N:26].[Na+].C([O-])(=O)C.[NH4+].[OH-].[Na+]>CO>[CH3:10][Si:9]([CH3:12])([CH3:11])[CH:8]([NH2:26])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67766280HCID 67766280, compound

Product 1

HCID 22399683HCID 22399683, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyltrimethylsilylketone (1.40 g, 7.3 mmol) of sodium cyanoborohydride (0.321 g, 5.1 mmol) and ammonium acetate (5.93 g, 73 mmol) in anhydrous methanol (25 ml) was stirred at room temperature for 48 hours. The mixture was poured into 2N sodium hydroxide (20 ml) and extracted with diethyl ether (3×100 ml). The organic phase was dried over anhydrous magnesium sulphate. Trituration, removal of the solvent, inuacuo, and chromatography from silica gel (ethyl acetate/cyclohexane 1:1) yielded the crude α-(trimethylsilyl)benzeneethanamine which was directly converted to the product of this step using 1 equivalent of (BOC)2O in THF. Rf: 0.74 (ethyl acetate/cyclohexane 1:1)

Workup

  1. extractionextracted with diethyl ether (3×100 ml)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customTrituration, removal of the solvent, inuacuo, and chromatography from silica gel (ethyl acetate/cyclohexane 1:1)

Sources & evidence

ORD record
ord-74f5f2e923044441bba1b0cd2b453e05
Source dataset
uspto-grants-1996_07
Patent number
US05532397

Reaction notes

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