Diethanolamine → HCID 53673682, compound

HRID 1768631Notes

Reaction equation

HRID 1768631 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[CH3:23][C:24]([NH:27][S:28]([C:31]1[S:39][C:38]2[S:37](=[O:41])(=[O:40])[N:36]([CH2:42][CH2:43][CH2:44][CH2:45][O:46][CH3:47])[CH2:35][C:34](=[O:48])[C:33]=2[CH:32]=1)(=[O:30])=[O:29])([CH3:26])[CH3:25].N(CCO)CCO>C1COCC1.C(OCC)(=O)C>[CH3:26][C:24]([NH:27][S:28]([C:31]1[S:39][C:38]2[S:37](=[O:40])(=[O:41])[N:36]([CH2:42][CH2:43][CH2:44][CH2:45][O:46][CH3:47])[CH2:35][C@@H:34]([OH:48])[C:33]=2[CH:32]=1)(=[O:30])=[O:29])([CH3:23])[CH3:25]

Participants

6

Reactant 3

HCID 8113DiethanolamineHCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)boraneHCID 22902007HCID 22902007, compound

Product 1

HCID 53673682HCID 53673682, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (+)-β-chlorodiisopinocamphenylborane (28.01 g, 0.087 mol) in THF (60 mL) at -20° C. was added a solution of the product from Step B (7.4 g, 0.017 mol) in THF (90 mL); this mixture was stirred for 40 hr while maintaining this temperature. Diethanolamine (9.13 g, 0.087 mol) was added to the reaction mixture which was allowed to warm to room temperature and stirred at this temperature for 2 hr. Evaporation of the THF gave a residue which was dissolved in ethyl acetate (100 mL); this solution was washed with water (100 mL). The aqueous layer was separated and extracted with ethyl acetate (3×50 mL). The ethyl acetate extracts were combined, washed with brine (2×20 mL), dried (MgSO4), and evaporated to a residue which was purified by column chromatography (silica, 60% ethyl acetate/hexane) to give an oil (6.4 g, 86%).

Workup

  1. temperaturewhile maintaining this temperature
  2. stirringstirred at this temperature for 2 hr
  3. customEvaporation of the THF
  4. customgave a residue which
  5. washthis solution was washed with water (100 mL)
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate (3×50 mL)
  8. washwashed with brine (2×20 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated to a residue which
  11. customwas purified by column chromatography (silica, 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a916df2ae8274e949c85437bd72936d4
Source dataset
uspto-grants-1995_01
Patent number
US05378703

Reaction notes

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