HCID 67189793, compound → HCID 67190813, compound

HRID 2355418Notes

Reaction equation

HRID 2355418 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][C@@H:8]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[F:29])[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:28][C:24]1[C:23]([F:29])=[C:22]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

HCID 67189793HCID 67189793, compound

Product 1

HCID 67190813HCID 67190813, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(R)-tert-butyl 3-((R)-(2-acetamidoethoxy)(3-chloro-2-fluorophenyl)methyl)piperidine-1-carboxylate (95 mg, 1.88 mmol) was dissolved in 20% v/v TFA/CH2Cl2 (8 mL) at 0° C., the mixture was allowed to warm to rt for 1 h and then concentrated in vacuo to give N-(2-((R)-(3-chloro-2-fluorophenyl)((R)-piperidin-3-yl)methoxy)ethyl)acetamide (63 mg, 87%), which was used without further purification. MS (E/Z): 329 (M+)

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-431ffbb5252040638096e17e10711427
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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