(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine

Base Information

• Chemical Name: (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine
• CAS No.: 960216-96-0
• Molecular Formula: C₂₀H₂₇NO
• Molecular Weight: 297.44

Synonyms:(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine

Chemical Property of (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine

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Technology Process of (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine

There total 2 articles about (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine 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: 77.0%

N-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}aniline (960216-84-6) → (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine (960216-96-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 55 ℃;

DOI:10.1016/j.tetasy.2007.09.018

Reference yield:

(1S,4R)-1,7,7-trimethyl-3-(phenylimino)bicyclo[2.2.1]heptan-2-one (24268-24-4,71681-62-4) → (1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine (960216-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / (i-PrO)3P / Pd(OAc)2 / toluene; tetrahydrofuran / 3 h / Heating

2: 77 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 55 °C

With lithium aluminium tetrahydride; triisopropyl phosphite; palladium diacetate; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/j.tetasy.2007.09.018

Reference yield: 45.0%

(1S,2R,3S,4R)-1,7,7-trimethyl-4'-methylene-N-phenyl-dihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-amine (960216-96-0) + 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine (1671-87-0) → (6R,9R,10S,11R,14S)-10-anilino-1,4-bis(pyridin-2-yl)-11:14-isopropylidene-14-methyl-2,3-diaza-8-oxadispiro[5.1.5.2]pentadeca-1,4-diene + (6S,9R,10S,11R,14S)-10-anilino-1,4-bis(pyridin-2-yl)-11:14-isopropylidene-14-methyl-2,3-diaza-8-oxadispiro[5.1.5.2]pentadeca-1,4-diene

Guidance literature:

In toluene; for 30h; Heating;

DOI:10.1016/j.tetasy.2007.11.012

upstream raw materials:

N-{(1S,2R,3E,4R)-1,7,7-trimethyl-4'-methylenedihydro-3'H-spiro[bicyclo[2.2.1]heptane-2,2'-furan]-3-ylidene}aniline

(1S,4R)-1,7,7-trimethyl-3-(phenylimino)bicyclo[2.2.1]heptan-2-one

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