Triethylamine → HCID 10293547, compound

HRID 1280724Notes

Reaction equation

HRID 1280724 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][CH:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15]2)[CH2:10][CH2:9]1.CCN(CC)CC.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:36]1([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:18][CH2:17][CH:16]([S:19]([C:22]4[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=4)(=[O:21])=[O:20])[CH2:15]3)[CH2:10][CH2:9]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 69927573HCID 69927573, compound

Product 1

HCID 10293547HCID 10293547, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(RS)-4-(1-Piperidin-4-yl-pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid (53.8 mg, 0.1 mmol), Et3N (50.5 mg, 0.5 mmol), phenylboronic acid (36.6 mg, 0.3 mmol) and copper(II) acetate (36 mg, 0.2 mmol) were suspensed in CH2Cl2 (2 ml). After 3.5 hours stirring at room temperature, the reaction mixture was directly chromatographed over silica gel (CH2Cl2—MeOH 98:2 then 95:5) to provide (RS)-4-[1-(1-phenyl-piperidin-4-yl)-pyrrolidine-3-sulfonyl]-phenol (10 mg, 26%) as a white foam, MS: m/e=387.3 (M+H+).

Workup

  1. customthe reaction mixture was directly chromatographed over silica gel (CH2Cl2—MeOH 98:2

Sources & evidence

ORD record
ord-641a6e12acfc49cf92e4c7c1a444cad0
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

Loading…