HCID 57659777, compound → HCID 57659771, compound

HRID 1011596Notes

Reaction equation

HRID 1011596 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:11]([CH:27]=[CH2:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C@H:11]([CH2:27][CH3:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 57659777HCID 57659777, compound

Product 1

HCID 57659771HCID 57659771, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (6) (0.663 g, 1.52 mmol) in EtOAc (5 ml) was added a small spatula tip of 10% Pd(C) and placed on Parr shaker under hydrogen at 45 PSI. The mixture was shaken under hydrogen overnight. After addition of more EtOAc the mixture was filtered through celite, and concentrated in vacuo to yield (2R,4R)-4-(tert-butyldimethylsilyloxy)-2-ethyl-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidine (7) (0.575 g, 86%) as a white crystalline solid. MS m/z 438.1 (M+H); retention time=6.841 min, method [10].

Workup

  1. filtrationwas filtered through celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ecbfe90f5646e7ab7c893e5c90afc1
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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