HCID 57988326, compound → HCID 57988339, compound

HRID 1666535Notes

Reaction equation

HRID 1666535 reaction equation
[CH2:1]([S:4]([C@:7]1([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:8]1)(=[O:6])=[O:5])[CH:2]=[CH2:3]>[Pd].CO>[C:29]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:31][C:26]([C@@:7]2([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:8]2)=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 57988326HCID 57988326, compound

Product 1

HCID 57988339HCID 57988339, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a vessel containing (2S,4R)-1-benzyl 2-methyl 4-(allylsulfonyl)-4-(biphenyl-4-yl)pyrrolidine-1,2-dicarboxylate (1.90 g, 3.66 mmol) and MeOH (100 mL) was added palladium/C (0.195 g, 0.183 mmol). The vessel was placed on Parr shaker under hydrogen with 25 psi pressure for 4 h. Quenched with CELITE®. Filtered, evaporated to afford the desired product (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-(propylsulfonyl)pyrrolidine-1,2-dicarboxylate (1.77 g, 3.39 mmol, 93% yield) as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 0.85-1.06 (m, 3 H) 1.64 (dt, J=14.87, 7.50 Hz, 2 H) 2.71-2.82 (m, 1 H) 3.01 (dt, J=13.05, 9.16 Hz, 1 H) 3.25-3.41 (m, 1 H) 3.60-3.84 (m, 3 H) 4.16-4.35 (m, 2 H) 4.69 (dd, J=11.42, 6.65 Hz, 1 H) 4.91-5.28 (m, 2 H) 7.14-7.43 (m, 6 H) 7.44-7.53 (m, 2 H) 7.63-7.88 (m, 6 H). LC-MS (retention time: 1.75 min, method A), MS m/z 522 (M+H).

Workup

  1. customQuenched with CELITE®
  2. filtrationFiltered
  3. customevaporated

Sources & evidence

ORD record
ord-39aefe18587e4c1584b1eb000706cfa9
Source dataset
uspto-grants-2011_10
Patent number
US08044023B2

Reaction notes

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