ChemicalBook CAS DataBase List (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester synthesis

12synthesis methods

Product Name:(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
CAS Number:361440-67-7
Molecular formula:C11H18N2O3
Molecular Weight:226.27

709031-38-9 Synthesis

1H-Pyrrole-1-carboxylic acid, 2-(aMinocarbonyl)-2,3-dihydro-, 1,1-diMethylethyl ester, (2S)-

709031-38-9
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Tetramethylammonium trifluoromethanesulfonate

25628-09-5
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(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

361440-67-7
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Yield:361440-67-7 93%

Reaction Conditions:

with n-butyllithium;C₄₀H₅₄NiP₂ in tetrahydrofuran;hexane at 0 - 20; for 16 h;Inert atmosphere;Reagent/catalyst;Solvent;

Steps:

5 Example 5: Preparation of the key intermediate (1S, 3S, 5S) -3- (aminocarbonyl) -2-azabicyclo [3.1.0] hexane-2-carboxylic acid tert-butyl ester(SM1)

In a dry three-necked flask, argon is protected. Adding ^ e40Tf (2. 2g), chiral nickel catalyst [(Ph3P)(TBu) 3P) Ni (CH2 (Ph) (Me) CH2)] (0.704 g) in anhydrous tetrahydrofuran (20 mL), cooled to 0 ° C,(S) -1-Ν-tert-butoxycarbonyl-2,3-dihydro-2-l-formamide (2. lg). And then under argon protection conditions,Slowly dropwise addition of n-butyllithium n-hexane solution (1.6111001 / 1,6.61 ^), after dripping, naturally rose to room temperature to continue to stirMix for 16 hours. A solution of undecane (1. OmL), n-pentane water (10 mL) was added from 200 mL of n-pentaneAnd 200mL of water mixed after standing stratification, take the middle layer of 10mL), stirring for 1 hour, standing stratified, organicThe phases were dried over magnesium sulfate overnight. Filtered and concentrated to give a colorless oil. The oil was on a silica gel column and the oil was madeThe mixture was homogenized in silica gel and eluted with n-hexane / ethyl acetate (20: 1) elution. The elution was complete and collectedAt the end of the product point, the eluent was concentrated under reduced pressure at 45 ° C to give a white solid, S (1S, 3S, 5S) -3- (aminocarbonylYl) -2-azabicyclo [3 · L 0] hexane-2-carboxylate (2 · lg, yield 93%). 66> 99%, (^> 99%.

References:

CN106554301,2017,A Location in patent:Paragraph 0040; 0041; 0042; 0043; 0044; 0045; 0046-0049

197142-36-2 Synthesis