tert-Butyl carbazate → HCID 88216559, compound

HRID 1521818Notes

Reaction equation

HRID 1521818 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([O:19][C:20](=[O:23])[NH:21][NH2:22])([CH3:18])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[C:15]([O:19][C:20]([NH:21]/[N:22]=[C:10]1/[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12][CH2:11]/1)=[O:23])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylate

Product 1

HCID 88216559HCID 88216559, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

1-Boc-3-piperidone (25 g; 125.47 mmol; 1.00 eq.) is dissolved in toluene (250 mL) to which tert-butyl-carbazate (16.58 g; 125.47 mmol; 1.00 eq.) is added and reaction mixture is heated to 60° C. for 4 hours. After this time reaction mixture is evaporated to dryness, taken up in ethyl acetate (100 mL) and heptane (100 mL), and the suspension is heated, then cooled down to rt and the suspension is filtered and dried to give 15 g (95%) of the title compound as a beige solid. MS (ESI−): 311.9.

Workup

  1. additionis added
  2. customreaction mixture
  3. customAfter this time reaction mixture
  4. customis evaporated to dryness
  5. temperatureheptane (100 mL), and the suspension is heated
  6. temperaturecooled down to rt
  7. filtrationthe suspension is filtered
  8. customdried

Sources & evidence

ORD record
ord-397d288127714041975bbebb80670d4f
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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