1-Diphenylmethoxy-2-formylamino-2-methylpropane → 1-Diphenylmethoxy-2-methyl-2-(methylamino)propane

HRID 1613189Notes

Reaction equation

HRID 1613189 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][C:10]([NH:13][CH:14]=O)([CH3:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][C:10]([CH3:12])([NH:13][CH3:14])[CH3:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 197753101-Diphenylmethoxy-2-formylamino-2-methylpropaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 197753221-Diphenylmethoxy-2-methyl-2-(methylamino)propaneYield 96.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-diphenylmethoxy-2-formylamino-2-methylpropane (8.2 g) in ether (50 ml) was added to a suspension of lithium aluminium hydride (2.2 g) in ether (100 ml) at a rate which maintained a gentle reflux. The mixture was stirred at room temperature for 18 hours, quenched by the sequential dropwise addition of water (2.2 ml), 5M aqueous sodium hydroxide solution (2.2 ml) and water (6.6 ml) and filtered. The filtrate was dried over sodium sulphate and evaporated to give the title compound as a colourless gum (7.5 g, 96%).

Workup

  1. temperaturemaintained a gentle reflux
  2. customquenched by the sequential dropwise addition of water (2.2 ml), 5M aqueous sodium hydroxide solution (2.2 ml) and water (6.6 ml)
  3. filtrationfiltered
  4. dry with materialThe filtrate was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-5701b48055a04608996cfde911c2e71b
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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