Tert-Butyl 6-(Hydroxymethyl)-3-Azabicyclo[3.1.0]Hexane-3-Carboxylate synthesis

7synthesis methods

Product Name:Tert-Butyl 6-(Hydroxymethyl)-3-Azabicyclo[3.1.0]Hexane-3-Carboxylate
CAS Number:850808-43-4
Molecular formula:C11H19NO3
Molecular Weight:213.27

871727-08-1 Synthesis

3-Azabicyclo[3.1.0]hexane-6-methanol, 3-(phenylmethyl)-

871727-08-1
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24424-99-5 Synthesis

24424-99-5
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Tert-Butyl 6-(Hydroxymethyl)-3-Azabicyclo[3.1.0]Hexane-3-Carboxylate

850808-43-4
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$55.00/25mg

Yield: 76%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 25; under 760.051 Torr; for 16 h;

Steps:

33D Example 33D tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
Example 33D
tert-butyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate
A mixture of EXAMPLE 33C (1.42 g, 7.0 mmol), Boc₂O (1.81 g, 8.4 mmol) and 10% Pd/C (200 mg) in methanol (80 mL) was hydrogenated at 25° C. for 16 h under H₂ (1 atm).
The mixture was filtered and the filtrate was evaporated to give the residue which was purified by chromatography to provide the title compound 4 (1.14 g, 76%). LCMS (ESI) m/z: 214 (M+1).

References:

HUMANWELL HEALTHCARE (GROUP) CO., LTD.;HUBEI BIO-PHARMACEUTICAL INDUSTRIAL TECHNOLOGICAL INSTITUTE INC.;MEDSHINE DISCOVERY INC.;WANG, Xuehai;DING, Zhaozhong;XU, Yong;CHEN, Shuhui;LI, Lie;LI, Gang;TU, Ronghua;WANG, Cailin;YUE, Yang;ZHANG, Zhibo;CHEN, Hailiang;SUN, Wenjie;HUANG, Lu US2017/29430, 2017, A1 Location in patent:Paragraph 0385