(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

Base Information

Chemical Name:(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane
CAS No.:1415098-82-6
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

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Chemical Property of (1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

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Technology Process of (1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

There total 4 articles about (1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane 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: 63.0%

: 1415098-72-4
(S)-1-benzyloxycarbonyl-6-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,3,6-tetrahydropyridine

: 1415098-82-6
(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

: 1415098-77-9
(1R,2R,6S)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

Guidance literature:: With potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Time; Overall yield = 100 %Spectr.;
DOI:10.1039/c2ob26732b

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 1415098-82-6
(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 5 steps

1.1: magnesium sulfate / diethyl ether / 2 h / 20 °C

2.1: boron trifluoride diethyl etherate / diethyl ether / 0.17 h / -20 °C / Inert atmosphere

2.2: -20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

4.1: Grubbs catalyst first generation / dichloromethane / 2 h / 20 °C

5.1: edetate disodium; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; potassium peroxymonosulfate / water; acetonitrile / 3 h / 0 °C

With Grubbs catalyst first generation; potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; magnesium sulfate; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1039/c2ob26732b

Reference yield:

: 1415098-65-5
N-{(S)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]allyl}-3-buten-1-amine

: 1415098-82-6
(1S,2R,6R)-3-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-oxa-3-azabicyclo[4.1.0]heptane

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

2: Grubbs catalyst first generation / dichloromethane / 2 h / 20 °C

3: edetate disodium; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; potassium peroxymonosulfate / water; acetonitrile / 3 h / 0 °C

With Grubbs catalyst first generation; potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; acetonitrile;
DOI:10.1039/c2ob26732b