tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate

Base Information

• Chemical Name: tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate
• CAS No.: 126301-09-5
• Molecular Formula: C₂₈H₃₉NO₆
• Molecular Weight: 485.621

Synonyms:tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate

Chemical Property of tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate

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Technology Process of tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate

There total 2 articles about tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate 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: 94.0%

dimethyl 2-benzylidenepropanedioate (6626-84-2) + tert-butyl ((1R,4R)-bornylideneamino)acetate (110269-68-6) → tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate (126301-09-5)

Guidance literature:

With n-butyllithium; tert-butyl alcohol; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1021/jo00008a052

Reference yield:

dimethyl 2-benzylidenepropanedioate (6626-84-2) + t-butyl (bornylideneamino)acetate (104505-09-1,110269-68-6,149250-52-2) → (2S,3R)-2-Methoxycarbonyl-3-phenyl-4-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester (126301-09-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 17 h;

Reference yield: 64.0%

tert-butyl 1,1-dimethyl (2R,3R)-3-<(1R,4R)-bornylideneamino>-2-phenyl-1,1,3-propanetricarboxylate (126301-09-5) → 2-tert-butyl methyl (2R,3R,4R)-3-phenyl-5-oxopyrrolidine-2,4-dicarboxylate (126301-14-2)

Guidance literature:

With hydroxylamine; acetic acid; In ethanol; for 4h; Heating;

DOI:10.1021/jo00008a052

upstream raw materials:

dimethyl 2-benzylidenepropanedioate

tert-butyl ((1R,4R)-bornylideneamino)acetate

t-butyl (bornylideneamino)acetate

Downstream raw materials:

2-tert-butyl methyl (2R,3R,4R)-3-phenyl-5-oxopyrrolidine-2,4-dicarboxylate

tert-butyl (2R,3S)-3-phenyl-5-oxopyrrolidine-2-carboxylate

(2R,3S,4R)-5-Oxo-3-phenyl-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester

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