Trifluoroacetic acid → (3R)-3-[(Benzylsulfinyl)methyl]pyrrolidine

HRID 1459722Notes

Reaction equation

HRID 1459722 reaction equation
[CH2:1]([S:8]([CH2:10][C@@H:11]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([S:8]([CH2:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54432698(3R)-3-(Benzylsulfinyl)methyl-1-(tert-butoxycarbonyl)pyrrolidine

Product 1

HCID 54013917(3R)-3-[(Benzylsulfinyl)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a similar method to that described in Example 93, step 2, (3R)-3-(benzylsulfinyl)methyl-1-(tert-butoxycarbonyl)pyrrolidine (0.2376 g, 0.735 mmol) was reacted with trifluoroacetic acid (1 ml) in dichloromethane (3 ml) to give, after work up, 0.1543 g (94%) of the title compound as a white solid, which was used without further purification. δH (250 MHz, CDCl3) 1.47 (1H, m), 2.09 (1H, m), 2.52-2.72 (4H, m), 2.94 (2H, m), 3.19 (1H, m), 3.96 (1H, d, J=12.9 Hz), 4.06 (1H, dd, J=12.9 and 3.6 Hz), 7.27-7.43 (5H, m).

Workup

  1. customto give
  2. customafter work up, 0.1543 g (94%) of the title compound as a white solid, which was used without further purification

Sources & evidence

ORD record
ord-52e8e0c050ec41fa9d382938717fde74
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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