Sodium Bromide → Tert-butyl 3-oxopiperidine-1-carboxylate

HRID 1260399Notes

Reaction equation

HRID 1260399 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+]>C1(C)C=CC=CC=1.O.CC1(C)N([O])C(C)(C)CCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 5456991-Boc-3-hydroxypiperidine2×HCID 23665760Sodium Hypochlorite

Product 1

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateYield 95.4%

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3-hydroxy-piperidine-1-carboxylic acid t-butyl ester (4.0 g, 20 mmol) synthesized in Section (1) was dissolved in a mixed solution (2:1:2, 100 mL) of toluene, water and ethyl ester, and 1.0 mol% TEMPO (31 mg), and NaBr (2.3 g) were sequentially added thereto. A mixture of NaHCO3 (4.7 g) and NaOCl (5%, 36 mL) was slowly added to the mixture under cooling conditions (0 to 4° C.). After the reaction was complete, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure to afford 3.8 g (yield: 95%) of the title compound.

Workup

  1. additionwere sequentially added
  2. additionwas slowly added to the mixture under cooling conditions (0 to 4° C.)
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtered organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-499f0d94087d469eb510a8f823c39591
Source dataset
uspto-grants-2013_06
Patent number
US08470836B2

Reaction notes

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