tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate

Base Information

• Chemical Name: tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate
• CAS No.: 139657-18-4
• Molecular Formula: C₃₁H₃₉N₃O₃
• Molecular Weight: 501.669

Synonyms:tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate

Chemical Property of tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate

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Technology Process of tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate

There total 5 articles about tricyclo<3.3.1.1^3,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate 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: 32.0%

L-Phenylalaninol (3182-95-4) + tricyclo<3.3.1.13,7>dec-2-yl (R)-<1-formyl-2-(1H-indol-3-yl)ethyl>carbamate (139657-17-3) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate (139657-18-4)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; for 2h; Ambient temperature;

DOI:10.1021/jm00086a017

Reference yield:

2-adamantyl chloroformate (53120-53-9) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate (139657-18-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 51 percent / NaHCO₃, NaOH / dioxane / 18 h / Ambient temperature

2: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) CH₂Cl₂, -15 deg C, 15 min 2.) CH₂Cl₂, a) -15 deg C, 1 h, b) RT, 15 h

3: 83 percent / lithium aluminum hydride / tetrahydrofuran / 30 h / 0 °C

4: 32 percent / sodium cyanoborohydride / methanol; acetic acid / 2 h / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; lithium aluminium tetrahydride; sodium cyanoborohydride; sodium hydrogencarbonate; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane; methanol; acetic acid;

DOI:10.1021/jm00086a017

Reference yield:

tricyclo<3.3.1.13,7>dec-2-yl <1-carboxy-2-(1H-indol-3-yl)ethyl>carbamate (139657-07-1) → tricyclo<3.3.1.13,7>dec-2-yl -<2-<<1-(hydroxymethyl)-2-phenylethyl>amino>-1-(1H-indol-3-yl)ethyl>carbamate (139657-18-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate / 1.) CH₂Cl₂, -15 deg C, 15 min 2.) CH₂Cl₂, a) -15 deg C, 1 h, b) RT, 15 h

2: 83 percent / lithium aluminum hydride / tetrahydrofuran / 30 h / 0 °C

3: 32 percent / sodium cyanoborohydride / methanol; acetic acid / 2 h / Ambient temperature

With 4-methyl-morpholine; lithium aluminium tetrahydride; sodium cyanoborohydride; isobutyl chloroformate; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1021/jm00086a017

upstream raw materials:

L-Phenylalaninol

tricyclo<3.3.1.1^3,7>dec-2-yl (R)-<1-formyl-2-(1H-indol-3-yl)ethyl>carbamate

2-adamantyl chloroformate

tricyclo<3.3.1.1^3,7>dec-2-yl <1-carboxy-2-(1H-indol-3-yl)ethyl>carbamate

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