Trifluoroacetic acid → HCID 69924259, compound

HRID 1280731Notes

Reaction equation

HRID 1280731 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[NH:8]1[CH2:12][CH2:11][C@@H:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69926446HCID 69926446, compound

Product 1

HCID 69924259HCID 69924259, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-3-(4-Hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.0 g, 10.2 mmol) in CH2Cl2 (36 ml) was treated with trifluoroacetic acid (7.8 ml, 0.1 mol). After 1 hour stirring at room temperature, the reaction mixture was concentrated to provide (R)-4-(pyrrolidin-3-yl-sulfanyl)-phenol trifluoroacetic acid (3.46 g) as an orange oil, MS: m/e=196.2 (M+H+) and [α]D20=+25.060 ° (c=1.2, MeOH).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0bdfbdc4bbe843059c802c12523aa161
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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