Diisopropylamine → HCID 14280468, compound

HRID 1763055Notes

Reaction equation

HRID 1763055 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[C:13](N)(=[O:16])[CH2:14][CH3:15].[NH:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21].CN(P(N(C)C)(N(C)C)=O)C.[CH3:36][CH:37]([CH:40]([O:46][CH:47]1[CH2:52][CH2:51][CH2:50][CH2:49][O:48]1)[CH:41]([CH3:45])[CH2:42][CH2:43][CH3:44])[CH2:38]I>O1CCCC1.O>[O:48]1[CH2:49][CH2:50][CH2:51][CH2:52][CH:47]1[O:46][CH:40]([CH:41]([CH3:45])[CH2:42][CH2:43][CH3:44])[CH:37]([CH3:36])[CH2:38][CH:14]([CH3:15])[C:13]([N:18]1[CH2:24][CH2:23][CH2:22][CH:19]1[CH2:20][OH:21])=[O:16]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 14280467HCID 14280467, compoundHCID 70363583HCID 70363583, compoundHCID 178418339Butyllithium

Product 1

HCID 14280468HCID 14280468, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
1 °C

Procedure

199 mg (1.97 mmol) of diisopropylamine was dissolved in 2.5 ml of dry tetrahydrofuran, and in an atmosphere of nitrogen, 0.795 ml of n-butyllithium (1.65N hexane solution) was added dropwise at 1° C., and the mixture was maintained at 1° C. for 45 minutes. To the reaction mixture were added dropwise at 1° C. 68.7 mg (0.438 mmol) of (S)-(-)-prolinol propionamide and 0.5 ml of dry tetrahydrofuran, and the mixture was reacted at room temperature for 1 hour. To the reaction mixture was added dropwise 0.2 ml (1.15 mmol) of dry HMPA, and the mixture was cooled to -100° C. Then, 112 mg (0.29 mmol) of the compound (8) was dissolved in 0.5 ml of dry tetrahydrofuran, and reacted at -100° C. for 11 hours, and left to stand at -80° C. for 4 days. Water was added to the reaction mixture, and the mixture was extracted with ether. The ethereal layer was washed with 1N hydrochloric acid and an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by chromatography (Wako Gel C-200 (3 g), hexane/ether/methanol) to give 97.0 mg (yield 86.6%) of compound (9).

Workup

  1. additionTo the reaction mixture were added dropwise at 1° C
  2. temperaturethe mixture was cooled to -100° C
  3. customreacted at -100° C. for 11 hours
  4. waitleft
  5. extractionthe mixture was extracted with ether
  6. washThe ethereal layer was washed with 1N hydrochloric acid
  7. dry with materialan aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by chromatography (Wako Gel C-200 (3 g), hexane/ether/methanol)

Sources & evidence

ORD record
ord-b676bf4d42d945aaa440f41b8b683b2d
Source dataset
uspto-grants-1989_05
Patent number
US04835292

Reaction notes

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