Diisopropylamine → HCID 70050443, compound

HRID 1720488Notes

Reaction equation

HRID 1720488 reaction equation
C(NC(C)C)(C)C.[C:8]1([CH3:17])[CH:13]=[CH:12][C:11]([S@:14]([CH3:16])=[O:15])=[CH:10][CH:9]=1.[CH2:18]([O:25][C:26]([N:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([N:32]1[CH2:38][CH2:37][CH2:36][C@H:33]1[CH:34]=[O:35])=[O:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[CH2:18]([O:25][C:26]([N:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([N:32]1[CH2:38][CH2:37][CH2:36][C@H:33]1[CH:34]([OH:35])[CH2:16][S@@:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:17])=[CH:9][CH:10]=1)=[O:15])=[O:31])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 122623Benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylateHCID 11170275(S)-(-)-Methyl p-tolyl sulfoxide

Product 1

HCID 70050443HCID 70050443, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To diisopropylamine (0.26 ml) in THF (6 ml) was dropwise added 1.62M n-butyllithium-hexane solution (1.12 ml) at -78° C., and the mixture was stirred at 0° C. for 0.5 hour. The reaction mixture was cooled to -30° C., dropwise added with (S)-(-)-methyl p-tolyl sulfoxide (255 mg) in THF (6 ml), and stirred at 0° C. for 0.5 hour. The reaction mixture was cooled to -78° C. and dropwise added with known N-benzyloxycarbonyl-L-prolyl-L-prolinal (300 mg) in THF (6 ml). After stirring for 0.5 hour, an aqueous solution of saturated ammonium chloride was added thereto, followed by stirring at room temperature for 10 minutes. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine order, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluate; chloroform-methanol) to give 388 mg of the title compound.

Workup

  1. customat -78° C.
  2. temperatureThe reaction mixture was cooled to -30° C.
  3. stirringstirred at 0° C. for 0.5 hour
  4. temperatureThe reaction mixture was cooled to -78° C.
  5. stirringAfter stirring for 0.5 hour
  6. stirringby stirring at room temperature for 10 minutes
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine order
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (eluate; chloroform-methanol)

Sources & evidence

ORD record
ord-3e6f706c851e499eb3d97ef7385fee51
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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