(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Base Information

Chemical Name:(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester
CAS No.:476371-58-1
Molecular Formula:C₂₁H₂₃NO₃
Molecular Weight:337.419
Hs Code.:

Synonyms:(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

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Chemical Property of (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

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Technology Process of (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

There total 7 articles about (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 476371-44-5
2-(benzyloxymethyl)-6-azabicyclo[3.1.0]hexane

: 476371-58-1
(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ja0258778

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 476371-58-1
(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran; dimethylformamide / 0.25 h / -40 °C

1.2: (+)-IPC₂BH / tetrahydrofuran / 48 h / -10 °C

1.3: 73 percent / aq. H₂O₂; NaOH / 12 h / 20 °C

2.1: 83 percent / pyridine / 12 h / 20 °C

3.1: 77 percent / LAH / diethyl ether / 20 h / Heating

4.1: 85 percent / tert-butyl hydroperoxide; TiCl₄ / CH₂Cl₂; various solvent(s) / 0.25 h / -78 °C

5.1: NaN₃; aq. NH₄Cl / methanol / 15 h / Heating

5.2: methane sulfonyl chloride; pyridine / 2 h / 20 °C

5.3: 84 percent / LAH / tetrahydrofuran / 5 h / 20 °C

6.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; titanium tetrachloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0258778

Reference yield:

: 110567-21-0
(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

: 476371-58-1
(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / pyridine / 12 h / 20 °C

2.1: 77 percent / LAH / diethyl ether / 20 h / Heating

3.1: 85 percent / tert-butyl hydroperoxide; TiCl₄ / CH₂Cl₂; various solvent(s) / 0.25 h / -78 °C

4.1: NaN₃; aq. NH₄Cl / methanol / 15 h / Heating

4.2: methane sulfonyl chloride; pyridine / 2 h / 20 °C

4.3: 84 percent / LAH / tetrahydrofuran / 5 h / 20 °C

5.1: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; titanium tetrachloride; ammonium chloride; triethylamine; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja0258778