(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

Base Information

Chemical Name:(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester
CAS No.:182138-21-2
Molecular Formula:C₂₆H₄₀N₂O₆Si
Molecular Weight:504.699
Hs Code.:

(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

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Chemical Property of (1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

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Technology Process of (1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

There total 5 articles about (1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl 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:

: 182137-75-3
(1S,4R)-3-Oxo-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

: 182138-21-2
(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) KHMDS / 1.) THF, room temperature, 15 min, 2.) THF, 4 deg C, 15 h; room temperature, 2 h.

2: H₂ / Pd/C / methanol / 12 h / 3102.9 Torr

3: 100 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h

4: 1.) molecular sieves, Et₃N, DPPA / 1.) toluene, 85 deg C, 2 h, 2.) 85 deg C, 12 h.

With lithium hydroxide; molecular sieve; diphenyl-phosphinic acid; hydrogen; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo960759m

Reference yield:

: (1S,4R)-3-[1-Methoxycarbonyl-meth-(Z)-ylidene]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

: 182138-21-2
(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 12 h / 3102.9 Torr

2: 100 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h

3: 1.) molecular sieves, Et₃N, DPPA / 1.) toluene, 85 deg C, 2 h, 2.) 85 deg C, 12 h.

With lithium hydroxide; molecular sieve; diphenyl-phosphinic acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo960759m

Reference yield:

: (1S,4R)-3-Hydroxy-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

: 182138-21-2
(1S,3S,4R)-3-[(2-Trimethylsilanyl-ethoxycarbonylamino)-methyl]-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C, 30 min; room temperature, 1 h.

2: 1.) KHMDS / 1.) THF, room temperature, 15 min, 2.) THF, 4 deg C, 15 h; room temperature, 2 h.

3: H₂ / Pd/C / methanol / 12 h / 3102.9 Torr

4: 100 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h

5: 1.) molecular sieves, Et₃N, DPPA / 1.) toluene, 85 deg C, 2 h, 2.) 85 deg C, 12 h.

With lithium hydroxide; molecular sieve; oxalyl dichloride; diphenyl-phosphinic acid; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo960759m