Triethylamine → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 1768605Notes

Reaction equation

HRID 1768605 reaction equation
[CH2:1](N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][C@H:16]([CH2:21][OH:22])[C@H:17]([CH2:19][CH3:20])C)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CS(C)=O>[C:8]([O:12][C:13]([NH:15][C@H:16]([CH:21]=[O:22])[CH2:17][CH:19]([CH3:20])[CH3:1])=[O:14])([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

Product 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateYield 101%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

9.59 ml (69.0 mmole) of triethylamine and 11.0 g (69.0 mmole) of a pyridine/sulfur trioxide complex were added to a solution of 5.0 g (23.0 mmole) of N-(t-butoxycarbonyl)-L-isoleucinol in 50 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 15 minutes. At the end of this time, the reaction mixture was poured onto ice-water, and extracted with diethyl ether. The organic extract was washed with a 5% w/v aqueous solution of citric acid, with a 5% w/v aqueous solution of sodium bicarbonate and with water, in that order. It was then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 5.0 g of N-(t-butoxycarbonyl)-L-leucinal as an oily substance.

Workup

  1. additionAt the end of this time, the reaction mixture was poured onto ice-water
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with a 5% w/v aqueous solution of citric acid, with a 5% w/v aqueous solution of sodium bicarbonate and with water, in that order
  5. dry with materialIt was then dried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-d485295a5d894570b4b4cd600964535c
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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