(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
CAS No.:577712-50-6
Molecular Formula:C₂₃H₂₉N₃O₃
Molecular Weight:395.502
Hs Code.:

Synonyms:(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

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Chemical Property of (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

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Technology Process of (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

There total 12 articles about (4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid 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: 62.0%

: 577712-02-8
(4R,9AR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 577712-50-6
(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Guidance literature:: (4R,9AR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester; With (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In toluene; for 0.5h;

benzyl alcohol; With sodium hydride; In toluene; at 70 ℃; for 3.5h;

Reference yield:

: 153305-67-0,100165-88-6,99646-28-3
tol-BINAP

: 577712-02-8
(4R,9AR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

: 100-51-6,185532-71-2
benzyl alcohol

: 577712-50-6
(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Guidance literature:: In toluene;

Reference yield:

: 221675-35-0
1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester

: 577712-50-6
(4R,9aR)-6-benzyloxy-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / DMAP / acetonitrile / 20 °C

2: 60 percent / m-CPBA / CH₂Cl₂ / 20 °C

3: 76 percent / ethyl chloroformate; HMDS / tetrahydrofuran / 20 °C

4: TFA / CH₂Cl₂ / 0 - 20 °C

5: NaH / dimethylformamide / 0 - 20 °C

6: TFA / CH₂Cl₂ / 0 - 20 °C

7: K₂CO₃ / methanol / 20 °C

8: LiAlH₄ / various solvent(s) / 0.25 h / Heating

9: CH₂Cl₂ / 20 °C

10: NaCNBH₃; AcOH / 20 °C

11: Pd₂(dba)3; (+/-)-BINAP; NaOH / toluene / 70 °C

With dmap; sodium hydroxide; lithium aluminium tetrahydride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; chloroformic acid ethyl ester; sodium hydride; sodium cyanoborohydride; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; acetic acid; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.bmcl.2005.11.083