Pyridine → 1,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamate

HRID 1108359Notes

Reaction equation

HRID 1108359 reaction equation
N1C=CC=CC=1.ClCCl.[C:10]([O:14][C:15]([NH:17][C@H:18]([CH2:23][OH:24])[C@H:19]([CH2:21][CH3:22])[CH3:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>CS(C)=O.O>[C:10]([O:14][C:15]([NH:17][C@@H:18]([C@@H:19]([CH3:20])[CH2:21][CH3:22])[CH:23]=[O:24])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

Product 1

HCID 113902721,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamateYield 92.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of pyridine--sulfur trioxide complex (5.1 g, 32 mmol) in dimethyl sulfoxide (20 ml)--dichloromethane (20 ml) was added dropwise a solution of (S)-N-(tert-butoxycarbonyl)-isoleucinol (1.4 g, 6.5 mmol) and triethylamine (3.2 g, 32 mmol) in dimethyl sulfoxide (20 ml)--dichloromethane (20 ml) under an argon gas stream and ice-cooling. After stirring for 30 minutes, the reaction solution was poured into water, and extracted with dichloromethane. The organic layer was washed with a saturated aqueous citric acid solution, an aqueous sodium bicarbonate solution, water and an aqueous sodium chloride solution, successively. After drying over sodium sulfate, the solvent was evaporated under reduced pressure to give (2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanal (1.3 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous citric acid solution
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-64a2feed5a0e4703b21f7444b2365e5c
Source dataset
uspto-grants-2000_05
Patent number
US06066672

Reaction notes

Loading…