HCID 59191713, compound → cis-1-Tert-butyl 3-methyl 2-(5-amino-2-(isopropylsulfonyl)phenyl)pyrrolidine-1,3-dicarboxylate

HRID 1515530Notes

Reaction equation

HRID 1515530 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C@H:16]1[C@@H: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.C1COCC1>[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]([C@H:16]2[C@@H: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

5

Reactant 1

HCID 59191713HCID 59191713, compound

Product 1

HCID 57942801cis-1-Tert-butyl 3-methyl 2-(5-amino-2-(isopropylsulfonyl)phenyl)pyrrolidine-1,3-dicarboxylateYield 103.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 10% palladium on carbon (1.3 g) was added 50F (5.7 g) in methanol (150 mL) and THF (50 mL) 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 for 4.0 h. The catalyst was filtered through Celite® and washed with methanol several times. The filtrate and the combined washings were evaporated and dried to give 5.5 g of 50G. 1H NMR (400 MHz, DMSO-d6, 100° C.) δ ppm 1.10 (d, J=6.60 Hz, 3H) 1.21-1.30 (m, 12H) 2.01-2.13 (m, 2H) 3.20 (s, 3H) 3.29-3.40 (m, 1H) 3.44-3.53 (m, 1H) 3.65 (ddd, J=10.17, 7.97, 5.50 Hz, 1H) 3.70-3.78 (m, 1H) 5.64 (d, J=8.25 Hz, 1H) 6.46-6.55 (m, 2H) 7.41 (d, J=7.70 Hz, 1H).

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-3749dd26951142aab0f31da9a72db98f
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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