Sodium Hydroxide → HCID 22399683, compound

HRID 1769951Notes

Reaction equation

HRID 1769951 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, in vacuo, 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) m.p. 67°-68° C.

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

Sources & evidence

ORD record
ord-752dffe772384bbd9d28db8fee22c8b1
Source dataset
uspto-grants-1995_01
Patent number
US05384312

Reaction notes

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