ChemicalBook CAS DataBase List TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE

TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE synthesis

4synthesis methods

Product Name:TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE
CAS Number:107259-06-3
Molecular formula:C9H15NO3
Molecular Weight:185.22

107017-73-2 Synthesis

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate

107017-73-2
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TERT-BUTYL (1-FORMYLCYCLOPROPYL)CARBAMATE

107259-06-3
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Yield:107259-06-3 99%

Reaction Conditions:

with oxalyl dichloride;triethylamine in dichloromethane;dimethyl sulfoxide at -78; for 1 h;

Steps:

214 tert-butyl 1 -formylcyclopropylcarbamate (3):
To a solution of oxalyl dichloride (277 mg, 2.2 mmol) in DCM (5 mL) was added DMSO (1 mL) and NEt3 (333 mg, 3.3 mmol). The resulting solution was stirred at -78C for lh. Then a solution of compound 2 (200 mg, 1.1 mmol) in 2 mL DCM was added. The reaction was stirred at -78 C for 1 h. Quenched by NH4C1 aq. and extracted by ethyl acetate. Organic layer was combined, dried over Na2SO4 and concentrated to give tert-butyl 1 -formylcyclopropylcarbamate (196 mg, 99%).

References:

ABBVIE INC.;MICHAELIDES, Michael;HANSEN, Todd;DAI, Yujia;ZHU, Guidong;FREY, Robin;GONG, Jane;PENNING, Thomas;CURTIN, Michael;MCCLELLAN, William;CLARK, Richard;TORRENT, Maricel;MASTRACCHIO, Anthony;KESICKI, Edward A.;KLUGE, Arthur F.;PATANE, Michael A.;VAN DRIE, John H. Jr.;JI, Zhiqin;LAI, Chunqiu C.;WANG, Ce WO2016/44770, 2016, A1 Location in patent:Page/Page column 717; 718

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