Trifluoroacetic acid → (3R)-3-[(4-Fluorobenzylsulfinyl)methyl]pyrrolidine

HRID 1459726Notes

Reaction equation

HRID 1459726 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][S:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][S:14]([CH2:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[O:15])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54513640(3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylsulfinyl)methyl]pyrrolidine

Product 1

HCID 53774999(3R)-3-[(4-Fluorobenzylsulfinyl)methyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a similar procedure to that described in Example 93, step 2, (3R)-1-(tert-butoxycarbonyl)-3-[(4-fluorobenzylsulfinyl)methyl}pyrrolidine (0.5149 g, 1.51 mmol) was reacted with trifluoroacetic acid (2ml) in dichloromethane (6ml) to give, after work up, 0.3447 g (95%) of the title compound as a white solid, which was used without further purification. δH (360 MHz, CDCl3) 1.57 (1H, m), 2.13 (1H, m), 2.54-2.72 (4H, m), 3.05 (2H, m), 3.27 (1H, m), 3.96 (2H, m), 708 (2H, t, J=8.6 Hz), 7.26-7.30 (2H, m).

Workup

  1. customto give
  2. customafter work up, 0.3447 g (95%) of the title compound as a white solid, which was used without further purification

Sources & evidence

ORD record
ord-6cc22a65e8c14a5e87ae74c7075e9fba
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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