exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol

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exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol Basic information
Product Name:exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol
Synonyms:exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol;exo-3-Cbz-3-azabicyclo[3....;Benzyl (1R,5S)-6-(hydroxyMethyl)-3-azabicyclo[3.1.0]hexan-3-carboxylate;benzyl (1S,5R)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate;Benzyl (1R,5S)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate;exo-Benzyl 6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate;benzyl rel-(1R,5S,6s)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate;3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6-(hydroxymethyl)-, phenylmethyl ester, (1α,5α,6α)-
CAS:134575-14-7
MF:C14H17NO3
MW:247.29
EINECS:
Product Categories:
Mol File:134575-14-7.mol
exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol Structure
exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol Chemical Properties
Boiling point 400.0±25.0 °C(Predicted)
density 1.265±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka14.94±0.10(Predicted)
Appearanceyellow oil
CAS DataBase Reference134575-14-7
Safety Information
MSDS Information
exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol Usage And Synthesis
Synthesis
Benzyl chloroformate

501-53-1

exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol

134575-14-7

2. Synthesis of [1α,5α,6α]-3-benzyloxycarbonyl-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexanes Benzyl ester of rel-(1R,5S,6r)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (1.0 g, 8.8 mmol) was dissolved in a mixed solvent of dioxane (40 mL) and water (40 mL). Sodium bicarbonate (3 g, 36 mmol) and benzyl chloroformate (1.3 mL, 9.1 mmol) were added sequentially. After 30 min of reaction, the reaction mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as an oil (2.15 g, 8.7 mmol, 99% yield). 1H NMR (CDCl3) δ: 7.32 (br s, 5H), 5.08 (s, 2H), 3.65 (m, 2H), 3.46 (m, 4H), 1.45 (m, 2H), 0.91 (m, 1H).

References[1] Patent: EP413455, 1991, A2
[2] Patent: WO2015/173225, 2015, A1
exo-3-Cbz-3-azabicyclo[3.1.0]hexane-6-methanol Preparation Products And Raw materials
Raw materials(1R,5S,6r)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate-->Benzyl chloroformate-->1,4-Dioxane-->Water-->Sodium bicarbonate
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