2-Amino-2-methyl-1-propanol → tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

HRID 636731Notes

Reaction equation

HRID 636731 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7](=O)([O:13]C(C)(C)C)[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>ClCCl>[C:9]([O:8][C:7]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:13])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 516892Sodium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-amino-2-methyl-1-propanol (921.2 mg, 10.33 mmol) in dichloromethane (5 ml) was cooled to 0° C. To the mixture was added a solution of di-t-butyl carbonate (Boc2O)(2.1045 g, 9.64 mmol) in dichloromethane (5 ml) dropwise for 30 minutes. After addition, the mixture was warmed to room temperature and stirred for 5 hours. The mixture was added to sat. NaHCO3 aqueous solution and extracted three times with ethyl acetate. The extract was dried over MgSO4 and concentrated to give the crude title compound (1.7204 g: 88%).

Workup

  1. additionAfter addition
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d82f92b01a684aa2976ab104e43f607c
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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