(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

Base Information

Chemical Name:(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester
CAS No.:891831-18-8
Molecular Formula:C₁₇H₂₅N₃O₅
Molecular Weight:351.403
Hs Code.:

(6-<i>tert</i>-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid <i>tert</i>-butyl ester

Synonyms:(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

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Chemical Property of (6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

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Technology Process of (6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

There total 23 articles about (6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic 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: 71.0%

: 891831-16-6
(4R,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexen-3-one

: 7677-24-9
trimethylsilyl cyanide

: 891831-18-8
(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

Guidance literature:: (4R,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexen-3-one; trimethylsilyl cyanide; With 1,5-cis,cis-cyclooctadiene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In tetrahydrofuran; at 60 ℃; for 65h;

With N-Bromosuccinimide; triethylamine; In tetrahydrofuran; at 4 ℃; for 1h;
DOI:10.1021/ja061696k

Reference yield:

: 1165952-92-0
cyclohexa-1,4-diene

: 891831-18-8
(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: 6.61 g / NaN₃; NH₄Cl / methanol; H₂O / 13 h / 60 °C

3.1: PPh₃ / acetonitrile / 2 h / 60 °C

3.2: 85 percent / triethylamine / acetonitrile / 1 h / -30 - -10 °C

4.1: chiral ligand; TMSN₃ / Y(OiPr)3 / various solvent(s) / 48 h / 20 °C

5.1: DMAP / acetonitrile / 3 h / 20 °C

5.2: 98 percent / NaOH / acetonitrile; H₂O / 2 h / 20 °C

6.1: PPh₃ / acetonitrile / 3 h / 50 - 60 °C

6.2: 90 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

7.1: Dess-Martin periodinane; SeO₂ / dioxane / 12 h / 80 °C

8.1: 330 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 4 °C

9.1: 1,5-cyclooctadiene / Ni(cod)2 / tetrahydrofuran / 65 h / 60 °C

9.2: 71 percent / NBS; triethylamine / tetrahydrofuran / 1 h / 4 °C

With dmap; selenium(IV) oxide; 1,5-cis,cis-cyclooctadiene; sodium azide; trimethylsilylazide; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; yttrium(III) isopropoxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja061696k

Reference yield:

: 6253-27-6
4,5-epoxy-cyclohexene

: 891831-18-8
(6-tert-butoxycarbonylamino-4-cyano-2-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 6.61 g / NaN₃; NH₄Cl / methanol; H₂O / 13 h / 60 °C

2.1: PPh₃ / acetonitrile / 2 h / 60 °C

2.2: 85 percent / triethylamine / acetonitrile / 1 h / -30 - -10 °C

3.1: chiral ligand; TMSN₃ / Y(OiPr)3 / various solvent(s) / 48 h / 20 °C

4.1: DMAP / acetonitrile / 3 h / 20 °C

4.2: 98 percent / NaOH / acetonitrile; H₂O / 2 h / 20 °C

5.1: PPh₃ / acetonitrile / 3 h / 50 - 60 °C

5.2: 90 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

6.1: Dess-Martin periodinane; SeO₂ / dioxane / 12 h / 80 °C

7.1: 330 mg / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 4 °C

8.1: 1,5-cyclooctadiene / Ni(cod)2 / tetrahydrofuran / 65 h / 60 °C

8.2: 71 percent / NBS; triethylamine / tetrahydrofuran / 1 h / 4 °C

With dmap; selenium(IV) oxide; 1,5-cis,cis-cyclooctadiene; sodium azide; trimethylsilylazide; ammonium chloride; Dess-Martin periodane; triphenylphosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; yttrium(III) isopropoxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja061696k