Hydrochloric Acid → 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester
Reaction equation
Cl.[OH-:2].[NH4+:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl>N1C=CC=CC=1>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=[N:3][OH:2])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Add ammonium hydroxide hydrochloride (50.68 mmol, 3.52 g, 2.00 equivalents) to a stirred solution of 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester (25.54 mol, 9.84 9, 1.00 equivalents) in pyridine (47.5 mL). Stir at room temperature overnight and at 70° C. for 4 hours. Cool the reaction mixture and add hydrochloric acid (3 M solution, 115 mL). Extract the reaction mixture with dichloromethane (115 mL), filter the organic layer, wash with water (100 mL), dry over magnesium sulfate, filter and evaporate. Recrystallize the resulting residue from toluene to yield a white solid (4.84 9). LC/MS (APCl), m/e 403 (MH+), retention time 2 min. 32 sec. Condition I.
Workup
- temperatureCool the reaction mixture
- extractionExtract the reaction mixture with dichloromethane (115 mL)
- filtrationfilter the organic layer
- washwash with water (100 mL)
- dry with materialdry over magnesium sulfate
- filtrationfilter
- customevaporate
- customRecrystallize the resulting residue from toluene
- customto yield a white solid (4.84 9)
- custom32 sec
Sources & evidence
- ORD record
- ord-c7abfad3610849669c669e3b7bb184fc
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550469B2
Reaction notes
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