1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 118383234, compound

HRID 2202764Notes

Reaction equation

HRID 2202764 reaction equation
[CH:1]1([C@H:7]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:9]([CH:19]=[O:20])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH:1]1([C@H:7]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C@@H:9]([CH:19]=[O:20])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 118382885HCID 118382885, compound2×

Product 1

HCID 118383234HCID 118383234, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4S)-tert-butyl 4-cyclohexyl-2-formylpyrrolidine-1-carboxylate (943 mg, 3.35 mmol) was treated with THF (20 mL) and DBU (1.0 mL, 6.70 mmol) and allowed to stir at room temperature overnight. The reaction mixture was concentrated to dryness on the rotovap, treated with DCM and a saturated solution of NH4Cl and extracted, washed with brine, dried over MgSO4, filtered and concentrated affording a mixture of crude (2S,4S)-tert-butyl 4-cyclohexyl-2-formylpyrrolidine-1-carboxylate and (2R,4S)-tert-butyl 4-cyclohexyl-2-formylpyrrolidine-1-carboxylate (470 mg, 1.67 mmol, 99% yield) as a clear, colorless viscous oil. MS (ESI) 304.1 [M+Na]+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness on the rotovap
  2. additiontreated with DCM
  3. extractiona saturated solution of NH4Cl and extracted
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customaffording

Sources & evidence

ORD record
ord-5dcf9c38de204dc589b841446a475f3f
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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