1-Iodododecane → HCID 86613070, compound

HRID 1644165Notes

Reaction equation

HRID 1644165 reaction equation
[H-].[Na+].[OH:3][C@H:4]([C@@H:10]([OH:16])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>CCCCC.CN(C=O)C>[CH2:18]([O:16][C@H:10]([C@@H:4]([O:3][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 202821-IodododecaneHCID 24758Sodium hydrideHCID 6610750N,N,N',N'-Tetramethyl-L-tartramide

Product 1

HCID 86613070HCID 86613070, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8003PentaneSolvent

Procedure

Sodium hydride (3.60 g, 60%, 90.0 mmol) was washed with pentane (3×) before DMF (150 ml) and (+)-(2R,3R)-2,3-dihydroxy-N,N,N′,N′-tetramethylsuccinamide (9.2 g, 45.0 mmol, origin: Aldrich) were added. The reaction mixture was left stirring at room temperature for 90 min, then a solution of 1-iodododecane (28.0 g, 94.5 mmol) in DMF (50 ml) was added. The reaction was left stirring for another 2 h at room temperature and then heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was extracted with ether (4×), washed with water (2×), dried (Na2SO4), and concentrated. Column chromatography (SiO2, dichloromethane/acetone 3:1) gave 5.93 g (28%) of a pale-yellow solid.

Workup

  1. additionwere added
  2. waitThe reaction mixture was left
  3. waitThe reaction was left
  4. stirringstirring for another 2 h at room temperature
  5. temperatureheated at 80° C. overnight
  6. temperatureAfter cooling to room temperature
  7. extractionthe reaction mixture was extracted with ether (4×)
  8. washwashed with water (2×)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4366b7385056448c9ca81df9d183fd5a
Source dataset
uspto-grants-2012_02
Patent number
US08124578B2

Reaction notes

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