Bromine → 1-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

HRID 1402665Notes

Reaction equation

HRID 1402665 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[Br:19]Br>O1CCCC1.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[CH:12]([Br:19])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24408BromineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidineYield 71.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-Oxo-piperidin-1-carboxylic acid tert-butyl ester (10 grams, 50 mmol) and aluminium chloride (0.67 grams, 5 mmol) in tetrahydrofuran (30 mL) and diethyl ether (30 mL) was cooled to 0° C., and then treated with bromine (2.6 mL, 50 mmol) over a period of 30 minutes. Stirred the reaction mass for 24 hours at 0-5° C. After completion of reaction, the obtain solids were filtered and the mother liquor was concentrated under vacuum. The obtain crude was triturated with diethyl ether and solids were filtered and dried under vacuum to obtain the title compound (10 grams).

Workup

  1. customAfter completion of reaction
  2. filtrationthe obtain solids were filtered
  3. concentrationthe mother liquor was concentrated under vacuum
  4. customThe obtain crude
  5. customwas triturated with diethyl ether and solids
  6. filtrationwere filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-cc27763676f14f6cbaaeda6679a18607
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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