Potassium Carbonate → (3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidine

HRID 1459723Notes

Reaction equation

HRID 1459723 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][SH:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][S:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 85171p-Fluorotoluene-alpha-thiolHCID 40479140(R)-tert-butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 54249072(3R)-1-(tert-Butoxycarbonyl)-3-[(4-fluorobenzylthio)methyl]pyrrolidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a similar method to that described in Example 93, step 1, (3R)-1-(tert-butoxycarbonyl)-3-[(methanesulfonyloxy)methyl]pyrrolidine (1.5000 g, 5.37 mmol) was reacted with 4-fluorobenzyl mercaptan (1.5511 g, 10.91 mmol) and potassium carbonate (1.1132 g, 8.05 mmol) in DMF (30 ml) at room temperature for 24 h to give 1.7507 g (100%) of the title compound as a colourless oil. δH (360 MHz, CDCl3) 1.45 (9H, s), 1.60 (1H, m), 2.00 (1H, m), 2.44 (2H, m), 2.97 (1H, m), 3.28 (1H, m), 3.46 (2H, m), 3.69 (2H, s), 7.00 (2H, t, J=8.6 Hz), 7.25-7.29 (2H, m). m/e (ES+) 348 (M+Na)+, 326 M+H)+, 270 (M-CMe3 +2H)+.

Sources & evidence

ORD record
ord-821bcbbdc2d148aaa02209309728c2d3
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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