Hydrochloric Acid → HCID 59376139, compound

HRID 2273866Notes

Reaction equation

HRID 2273866 reaction equation
Cl.O1CCOCC1.[CH2:8]([O:10][C:11]([C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[C@H:14]1[C:28]1[CH:33]=[CH:32][C:31]([NH:34]C(OC(C)(C)C)=O)=[CH:30][CH:29]=1)=[O:12])[CH3:9].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:8]([O:10][C:11]([C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[C@H:14]1[C:28]1[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=1)=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 59376160HCID 59376160, compound

Product 1

HCID 59376139HCID 59376139, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4N HCl in 1,4-dioxane (5 mL, 20 mmol) was slowly added to a 0° C. solution of the above crude product (2R,3S)-2-(4-tert-Butoxycarbonylaminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester (840 mg, 1.72 mmol) in dry CH2Cl2 (4 mL). After the addition of the HCl, the reaction mixture was allowed to attain r.t and stirred for 1 h. It was diluted with CH2Cl2 (30 mL), cooled to 0° C. and neutralized with saturated aqueous NaHCO3 to get the (2R,3S)-2-(4-aminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester (612 mg) in 97% yield over two steps.

Sources & evidence

ORD record
ord-6e5e55832c4e4fcb942c3a8237358c44
Source dataset
uspto-grants-2015_09
Patent number
US09126939B2

Reaction notes

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