Hydrochloric Acid → 4-[1-(3-Bromo-5-methoxymethyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 456530Notes

Reaction equation

HRID 456530 reaction equation
Cl.[NH2:2][OH:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][C:21]([CH2:25][O:26][CH3:27])=[CH:22][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][C:21]([CH2:25][O:26][CH3:27])=[CH:22][C:23]=2[Br:24])=[N:2][OH:3])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 588176604-[1-(3-Bromo-5-methoxymethyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 724345774-[1-(3-Bromo-5-methoxymethyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl esterYield 96.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add hydroxylamine hydrochloride (2.29 g, 45.27 mmol, 2.00 equivalents) to a stirred solution of 4-[1-(3-bromo-5-methoxymethyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester (9.47 g, 22.64 mmol, 1.00 equivalents) in pyridine (42.40 mL). Stir the resulting solution at room temperature overnight and then at 70° C. for 4 hours. Cool the reaction mixture slightly, add hydrochloric acid (3N, 100 mL) and extract the resulting mixture with dichloromethane (100 mL). Wash the extract with water (100 mL), dry over magnesium sulfate, filter and evaporate to yield the desired product as a yellow oil (9.48 g).

Workup

  1. waitat 70° C. for 4 hours
  2. temperatureCool the reaction mixture slightly
  3. extractionextract the resulting mixture with dichloromethane (100 mL)
  4. washWash the
  5. extractionextract with water (100 mL)
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. customevaporate

Sources & evidence

ORD record
ord-ee5c52546737425587bd088fc3cccefa
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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