1-tert-Butyl 3-methyl 2-(2-(isopropylsulfonyl)-5-nitrophenyl)pyrrolidine-1,3-dicarboxylate → HCID 57942794, compound

HRID 1438114Notes

Reaction equation

HRID 1438114 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH:16]1[CH:20]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][CH2:18][N:17]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])(=[O:6])=[O:5])([CH3:3])[CH3:2]>[Pd].CO>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[C:8]([CH:16]2[CH:20]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][CH2:18][N:17]2[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH:9]=1

Participants

4

Reactant 1

HCID 579428471-tert-Butyl 3-methyl 2-(2-(isopropylsulfonyl)-5-nitrophenyl)pyrrolidine-1,3-dicarboxylate

Product 1

HCID 57942794HCID 57942794, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To palladium on carbon (0.5 g) was added 20E in methanol (50 mL) carefully under a stream of nitrogen. The vessel was flushed and degassed with nitrogen gas (3×) and a balloon containing hydrogen gas was introduced. The reaction was stirred at rt overnight. The catalyst was filtered through celite and washed with methanol several times. The filtrate and the combined washings were evaporated and dried to give 2.0 g of crude 20F.

Workup

  1. customThe vessel was flushed
  2. customdegassed with nitrogen gas (3×)
  3. additiona balloon containing hydrogen gas
  4. additionwas introduced
  5. filtrationThe catalyst was filtered through celite
  6. washwashed with methanol several times
  7. customThe filtrate and the combined washings were evaporated
  8. customdried

Sources & evidence

ORD record
ord-72dbfcbac83646ad84832777c5905e6b
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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