Hydrochloric Acid → 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 456524Notes

Reaction equation

HRID 456524 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

HCID 313Hydrochloric AcidHCID 13908798HCID 13908798, compoundHCID 588177114-[1-(3-Bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 724345734-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl EsterYield 23.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 g, 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 g). LC/MS (APCI), m/e 403 (MH+), retention time 2 min. 32 sec. Condition I.

Workup

  1. temperatureCool the reaction mixture
  2. extractionExtract the reaction mixture with dichloromethane (115 mL)
  3. filtrationfilter the organic layer
  4. washwash with water (100 mL)
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate
  8. customRecrystallize the resulting residue from toluene

Sources & evidence

ORD record
ord-a4c08d3300a647d4ba825fffd3ff538f
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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