ChemicalBook CAS DataBase List tert-butyl N-(3-hydroxy-3-methylcyclobutyl)carbamate

tert-butyl N-(3-hydroxy-3-methylcyclobutyl)carbamate synthesis

4synthesis methods

Product Name:tert-butyl N-(3-hydroxy-3-methylcyclobutyl)carbamate
CAS Number:1427329-27-8
Molecular formula:C10H19NO3
Molecular Weight:201.26

(1-Oxa-spiro[2.3]hex-5-yl)-carbamic acid tert-butyl ester

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tert-butyl N-(3-hydroxy-3-methylcyclobutyl)carbamate

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Yield:1427329-27-8 94%

Reaction Conditions:

with lithium triethylborohydride in tetrahydrofuran at 0; for 3 h;Inert atmosphere;

Steps:

D D. tert-Butyl (3-hydroxy-3-methylcyclobutyl)carbamate

Lithium triethylborohydride (34.8 mL, 34.8 mmol) in THE (1 .0 M) was added to tert-butyl 1-oxaspiro[2.3]hexan-5-ylcarbamate (Intermediate 21C) (5.34 g, 26.8 mmol) in THE (89 mL) at0 °C under nitrogen. After 3 h, reaction mixture was quenched with water, solid potassium carbonate was added, then extracted with diethyl ether, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with EtOAc:hexanes (2:3 to 1:1) to give the title compound (5.36 g, 94% yield). 1H NMR (400 MHz, CD3SOCD3) 1.17 (5, 1.5 H), 1.19 (5, 1.5 H), 1.35 (5, 9 H), 1.78-1.92 (m, 2 H), 2.08-2.18 (m, 2H), 3.46 (h, J = 8Hz, 0.5 H), 3.99 (h, J = 8Hz, 0.5 H), 4.70 (brs, 0.5 H), 4.83 (brs, 0.5 H), 7.00 (d, J = 6 Hz, I H); LC-MS (ES-MS) M+H = 202.

References:

WO2018/69863,2018,A1 Location in patent:Page/Page column 129

Carbamic acid, (3-methylenecyclobutyl)-, 1,1-dimethylethyl ester (9CI)

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References

15760-36-8 Synthesis

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15760-35-7 Synthesis

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