HCID 22244954, compound → HCID 22244957, compound

HRID 891224Notes

Reaction equation

HRID 891224 reaction equation
[C:1]([O:5][CH2:6][C:7]([CH3:13])([N+:10]([O-])=O)[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1(C)C=CC=CC=1.[Ni]>[NH2:10][C:7]([CH3:13])([CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:8][OH:9]

Participants

5

Reactant 2

HCID 22244954HCID 22244954, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22244957HCID 22244957, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 150 g (0.78 mol) of 3-tert-butoxy-2-methyl-2-nitro-propan-1-ol [prepared according to Example 1c or 1c′] in 700 ml of toluene in a pressure vessel is added 15 g of Raney-Ni and 40 ml of a pH 7.00 buffer [NORMEX (RTM), Carlo Erba]. Through the closed autoclave is added at room temperature hydrogen under 50-60 bar pressure. The reaction mixture is heated to 40° C. and maintained at this temperature for 8 hours. The reaction mixture is then cooled to room temperature, diluted with toluene, filtered and the filtrate concentrated using a vacuum rotary evaporator. The residue yields 2-amino-3-tert-butoxy-2-methyl-propan-1-ol (compound 301, Table 1), pale green solid, m.p. 30-35° C.

Workup

  1. temperaturemaintained at this temperature for 8 hours
  2. temperatureThe reaction mixture is then cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customa vacuum rotary evaporator

Sources & evidence

ORD record
ord-dfb8ef1c5f7a457b9f7dca395a9ce354
Source dataset
uspto-grants-2006_02
Patent number
US07002010B2

Reaction notes

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