Sodium Thiosulfate → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 1725196Notes

Reaction equation

HRID 1725196 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 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 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (2-hydroxy-1,1-dimethylethyl)-carbamic acid tert-butyl ester (284 mg, 1.5 mmol) in CH2Cl2 (5 mL) was added at 0° C. Dess-Martin periodane (763 mg, 1.8 mmol). After 1.5 h, a solution of 0.26M Na2S2O3 in saturated NaHCO3 (6 mL) was added and the resulting mixture was stirred for 15 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated to yield (1,1-dimethyl-2-oxo-ethyl)carbamic acid tert-butyl ester as a white solid which was used in the next step without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a333a3f2f1d44c6ebf3da2fc978695f7
Source dataset
uspto-grants-2009_02
Patent number
US07488848B2

Reaction notes

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