Pyrrolidine → HCID 178474509, compound

HRID 2245367Notes

Reaction equation

HRID 2245367 reaction equation
Cl[CH2:2][C:3]1[S:7]/[C:6](=[N:8]\[C:9](=[O:11])[CH3:10])/[N:5]([C:12]2[CH:22]=[CH:21][C:15]3[O:16][C:17]([F:20])([F:19])[O:18][C:14]=3[CH:13]=2)[CH:4]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[F:19][C:17]1([F:20])[O:16][C:15]2[CH:21]=[CH:22][C:12]([N:5]3[CH:4]=[C:3]([CH2:2][N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)[S:7]/[C:6]/3=[N:8]\[C:9](=[O:11])[CH3:10])=[CH:13][C:14]=2[O:18]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 178474507HCID 178474507, compound

Product 1

HCID 178474509HCID 178474509, compound

Procedure

The allyl chloride (Example 24A, 16 mg, 46 μmol) was dissolved into pyrrolidine (200 μL) and stirred 10 minutes. Then the mixture was twice diluted with and concentrated from EtOAc, and partitioned between 2:1 EtOAc/hexanes (1.5 mL) and water (1 mL). The organic phase was separated and washed with water, dried (Na2SO4), and chromatographed on silica (2 to 5% MeOH/CH2Cl2) to give the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.81 (4H), 2.22 (3H), 2.60 (4H), 3.66 (2H), 6.91 (1H), 7.17 (2H), 7.36 (1H); MS (ESI) 382 (M+H)+.

Workup

  1. additionThen the mixture was twice diluted with and
  2. concentrationconcentrated from EtOAc
  3. custompartitioned between 2:1 EtOAc/hexanes (1.5 mL) and water (1 mL)
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customchromatographed on silica (2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-67850c91f42847c0abe79d9cbf3066e0
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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