Methanol → HCID 14102971, compound

HRID 969186Notes

Reaction equation

HRID 969186 reaction equation
O[C:2]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.FC(F)(F)C(O)=O.C(Cl)Cl.CO.[H][H]>[Pd]>[C:18]1([C@@H:2]2[CH2:6][NH:5][C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86602285HCID 86602285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14102971HCID 14102971, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-tert-Butyl 2-methyl (2S)-4-hydroxy-4-phenylpyrrolidine-1,2-dicarboxylate (0.32 g, 0.0010 mol) was treated with trifluoroacetic acid (1.00 mL, 0.0130 mol) and methylene chloride (1.00 mL, 0.0156 mol) at rt for 4 h. The solvents were evaporated and the residue was dissolved in methanol (5.0 mL, 0.12 mol). Palladium (50.0 mg, 0.000470 mol) was added under nitrogen and the resulting mixture was hydrogenized with a hydrogen-gas-filled-balloon for 3 h. The mixture was filtered and the filtrate was concentrated to give the desired product, which was directly used in the next step without further purification.

Workup

  1. customThe solvents were evaporated
  2. additiongas-filled-balloon for 3 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9ffce3c280534d4c8f7956f6a4b3d732
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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