ChemicalBook CAS DataBase List 1-Cbz-4-Piperidone

1-Cbz-4-Piperidone synthesis

14synthesis methods

Product Name: 1-Cbz-4-Piperidone
CAS Number:19099-93-5
Molecular formula:C13H15NO3
Molecular Weight:233.26

1-Z-4-Piperidone is the starting material in biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol condensation reactions. 1-(Benzyloxycarbonyl)-4-piperidinone is the starting material in biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol condensation reactions. 1-(Benzyloxycarbonyl)-4-piperidinone is synthesized starting from the reaction of 4-Piperidone monohydrate hydrochloride and potassium carbonate, then added with carbonic acid benzyl ester 2,5-dioxo-pyrrolidin-1-yl ester solution and concentrated to extract into EtOAc, washed with 5% aqueous citric acid, saturated NaHC03 solution and brine, dried (MgS04), filtered and concentrated to yield benzyl 4-oxopiperidine-1-carboxylate.

501-53-1
395 suppliers
$10.00/1g

19099-93-5
324 suppliers
$5.00/1g

Yield:19099-93-5 85%

Reaction Conditions:

Stage #1:4-piperidone hydrochloride with N-ethyl-N,N-diisopropylamine in dichloromethane;water at 0; for 0.0833333 h;
Stage #2:benzyl chloroformate in dichloromethane;water at 0 - 20; for 2.33333 h;

Steps:

1
Example 1;. N-Benzyloxycarbonyl-4-oxopiperidine (E-1);. A stirred solution of 4-oxopiperidine hydrochloride monohydrate (1.0 g, 6.5 mmol) in dry dichloromethane (DCM, 40 mL) was cooled to 0°C, treated with diisopropylethylamine (3.40 mL, 19.5 mmol), stirred for five minutes, treated over 20 minutes with benzyl chloroformate (1.54 mL, 10.7 mmol) over 20 minutes, allowed to warm to room temperature and stirred for two hours. The mixture was partitioned between DCM (25 mL) and water (15mL). The layers were separated and the aqueous phase was extracted with DCM (2 x 25 mL). The combined organic phases were washed with brine (1 x 15 mL), dried over Na2S04 and evaporated to a residue that was purified by column chromatography using a gradient of 20 to 40 % EtOAc in hexanes as eluant. Evaporation of the collected fractions gave carbamate E-1 (1.20 g, 85 %) as a clear oil: HRMS calc'd for C13Hl5NO3 (M+) : 233. 1051, found: 233.1048 ; 1H NMR (CDC13) 8 2.43 (s, 4H), 3.78 (d, 4H, J= 5.96), 5.16 (s, 2H), 7. 35 (m, 5H).

References:

BIOAXONE THERAPEUTIQUE INC. WO2005/80394, 2005, A1 Location in patent:Page/Page column 122

FullText

41979-39-9 Synthesis

41979-39-9
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501-53-1
395 suppliers
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19099-93-5
324 suppliers
$5.00/1g

References

13139-17-8
497 suppliers
$6.00/25g

40064-34-4
373 suppliers
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19099-93-5
324 suppliers
$5.00/1g

References

95798-23-5 Synthesis

Benzyl 4-hydroxy-1-piperidinecarboxylate

95798-23-5
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19099-93-5
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$5.00/1g

References

8-(BENZYLOXYCARBONYL)-1,4-DIOXA-8-AZASPIRO[4.5]DECANE

139524-58-6
11 suppliers
$640.00/5g

19099-93-5
324 suppliers
$5.00/1g

References

1-Cbz-4-Piperidone Related Search:

N-Carbethoxy-4-piperidone 2-Piperidone Trimethoprim Benzyl alcohol DROPERIDOL Thalidomide tert-Butyl carbazate Benzyl benzoate 1-BENZYL 4-ETHYL PIPERIDINE-1,4-DICARBOXYLATE N-Cbz-Nortropinone