Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

HRID 452013Notes

Reaction equation

HRID 452013 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH3:29])=[O:27])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31].C(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[O:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[O:28][CH3:29])[CH:5]=[CH:6][CH:7]=1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 595984981-Piperidinecarboxylic acid, 3-[(R)-(3-chlorophenyl)[2-[(methoxycarbonyl)amino]ethoxy]methyl]-, 1,1-dimethylethyl ester, (3R)-

Product 2

HCID 6422Trifluoroacetic acidYield 100%HCID 59598478Carbamic acid,N-[2-[(R)-(3-chlorophenyl)(3R)-3-piperidinylmethoxy]ethyl]-,methyl ester

Procedure

(R)-tert-Butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate (4.86 g, 11.4 mmol) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (10 mL). The reaction mixture was stirred at rt for 1 hr. The solvent was removed in vacuo to afford methyl 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate as TFA salt (4.8 g, 100%), which was used for the next step directly without purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-edd5b7865b52477b9f185d2527c1a14b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…