Sodium Thiosulfate → Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate

HRID 130319Notes

Reaction equation

HRID 130319 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([NH:30][C@H:31]([CH2:35][OH:36])[CH:32]([CH3:34])[CH3:33])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(OCC)C>[C:26]([O:25][C:23](=[O:24])[NH:30][CH:31]([CH:35]=[O:36])[CH:32]([CH3:33])[CH3:34])([CH3:27])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

Product 1

HCID 545985Tert-butyl 3-methyl-1-oxobutan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (3.12 g, 0.0073 mol, 1.5 eq) in dichloromethane (25 mL) was added a solution of N-Boc-L-valinol (1 g, 0.0049 mol, 1 eq) in dichloromethane (25 mL). The reaction mixture was stirred at room temperature for 3 h and was diluted with diethyl ether (50 mL). The mixture was poured into an aqueous saturated solution of sodium bicarbonate (100 mL) containing sodium thiosulfate (8.16 g, 10.5 eq). The mixture was stirred for 30 min and the layers were separated. The ether layer was washed with an aqueous saturated solution of sodium bicarbonate (50 mL), water (50 mL), dried (sodium sulfate) and filtered. The filtrate was concentrated to give the crude (1-formyl-2-methyl-propyl)-carbamic acid tert-butyl ester used for the next step without further purification.

Workup

  1. stirringThe mixture was stirred for 30 min
  2. customthe layers were separated
  3. washThe ether layer was washed with an aqueous saturated solution of sodium bicarbonate (50 mL), water (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b2bbff4dfa654deba2c5b6dd9e1709e8
Source dataset
uspto-grants-2008_06
Patent number
US07381721B2

Reaction notes

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