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

HRID 1968885Notes

Reaction equation

HRID 1968885 reaction equation
[C:1]([NH:8][C@H:9]([CH2:14][OH:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C>CS(C)=O.C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][C@H:9]([CH:14]=[O:15])[C@@H:10]([CH3:11])[CH2:12][CH3:13])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

Product 1

HCID 113902721,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamateYield 103%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of Boc-isoleucinol (3.89 g, 17.9 mmol) in DMSO (15 mL) and DCM (200 mL) was added DIEA (9.7 mL, 55.5 mmol), followed by dropwise addition of a solution of Py.SO3 (8.83 g, 55.5 mmol) in DMSO (50 mL, +10 mL to rinse the funnel). The reaction mixture was stirred at rt for 2 h. After removal of the DCM, the residue was diluted with Et2O (400 mL) and washed with H2O (2×100 mL) and brine (150 mL). The aqueous layer was back extracted with Et2O (100 mL). The combined Et2O layer was washed with saturated NaHCO3 (150 mL) and dried (Na2SO4). The solvent was removed to give the titled compound (3.97 g).

Workup

  1. washto rinse the funnel)
  2. customAfter removal of the DCM
  3. additionthe residue was diluted with Et2O (400 mL)
  4. washwashed with H2O (2×100 mL) and brine (150 mL)
  5. extractionThe aqueous layer was back extracted with Et2O (100 mL)
  6. washThe combined Et2O layer was washed with saturated NaHCO3 (150 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-9116bdff4e594ca79284afbe67772e9e
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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