ChemicalBook CAS DataBase List tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate synthesis

3synthesis methods

Product Name:tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate
CAS Number:1181816-12-5
Molecular formula:C11H17NO3
Molecular Weight:211.26

A solution of crude tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate (1.00 g,4.69mmol, 1.00 equiv) in dichloromethane(20 mL) was treated with Dess-Martin periodinane(2.10g,4.95 mmol, 1.06 equiv) in two batches a few min apart at 0 °C. After 10 min, the ice bath wasremoved, and the reaction was monitored by TLC (50% ethyl acetate, PMA stain). After 30 min.the reaction was diluted with ethyl acetate and washed twice with satd sodium bicarbonate. Theorganic layer was dried over sodium sulfate, filtered, and concentrated. The crude product waspurified by flash chromatography (80g silica gel, 10 to 50% ethyl acetate/heptane; pure fractionswere identified by TLC with PMA stain; an unidentified impurity elutes slightly earlier than theproduct) to give tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate as a white solid (721 mg,73%). mp 114.5-116C.

1239320-10-5 Synthesis

tert-butyl 5,5-dichloro-6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

1239320-10-5
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tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

1181816-12-5
184 suppliers
$9.00/100mg

Yield:1181816-12-5 66%

Reaction Conditions:

with ammonium chloride;zinc in methanol at 20; for 18 h;Inert atmosphere;

Steps:

1.3 Step 3: tert-Butyl-6-oxo-2-oxaspiro [3.3] heptane-2-carboxylic acidTert-butyl ester

Butyl-5,5-dichloro-6-oxo-2-azaspiro [3.3] heptane-2-carboxylic acid tert-butyl ester (1.65 g, 5.89 mmol, 1.0 eq)Zinc powder (0.85 g, 15.0 mmol, 2.6 eq)Ammonium chloride (1.2 g, 22.0 mmol, 3.8 eq) was added to methanol (30 mL) and reacted at room temperature for 18 h under nitrogen. After completion of the reaction, water (40 mL) was added, EA (30 mL x 2) was extracted, dried, , PE: EA (v / v) = 5: 1 column chromatography to give 0.8 g of product as a white solid in 66.0% yield.

References:

CN106565706,2017,A Location in patent:Paragraph 0176; 0177; 0178

1147557-97-8 Synthesis

tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

1147557-97-8
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$14.00/100mg

1181816-12-5
184 suppliers
$9.00/100mg

References

1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester

934664-41-2
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$20.00/1g

1181816-12-5
184 suppliers
$9.00/100mg

References

tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate Related Search:

Carbamic acid, N-(trans-3-aminocyclobutyl)-, 1,1-dimethylethyl ester 1-BOC-3-METHYLAMINOAZETIDINE 1-Piperidinecarboxylicacid,2-methyl-4-oxo-,1,1-dimethylethylester,(2S)-(9CI) 1-BOC-4-FLUORO-4-(HYDROXYMETHYL)-PIPERIDINE 1-Piperidinecarboxylicacid,2-methyl-4-oxo-,1,1-dimethylethylester,(2R)-(9CI) 6-bromo-pyridine-2-carboxylic acid tert-butyl ester tert-butyl 6-oxo-2-azaspiro[4.4]nonane-2-carboxylate(WX101410)