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

HRID 1264036Notes

Reaction equation

HRID 1264036 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(N(CC)CC)C.CS(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution 2-(tert-Butoxycarbonylamino)-2-methyl-1-propanol (5.7 g, 30.0 mmol) in triethylamine (42 mL) was added a mixture of sulfur trioxide pyridine complex (14.3 g, 90.0 mmol) in anhydrous DMSO (dimethylsulfoxide) (50 mL) at room temperature. The reaction was stirred for 1 hour under nitrogen and concentrated. The residue was dissolved in EtOAc (200 mL), washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, and concentrated to give crude 2-(tert-butoxycarbonylamino)-2-methyl propionaldehyde as yellow oil. Purification by distillation afforded 4.90 g (87%) of waxy, white solid: 1H NMR (CDCl3) δ 1.30 (s, 6H), 1.41 (s, 9H), 4.97 (br, 1 H), 9.40 (s, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washwashed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5da599e80c234a5f939942c33d51d402
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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