(S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate

Base Information

• Chemical Name: (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate
• CAS No.: 1169852-67-8
• Molecular Formula: C₂₄H₂₁NO₂
• Molecular Weight: 355.436
• Mol file: 1169852-67-8.mol

Synonyms:(S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate

Chemical Property of (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate

There total 4 articles about (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate 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: 57.0%

fluorenyl carbamate (1001754-55-7) + cinnamyl tert-butyl carbonate (124517-47-1) → (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate (1169852-67-8)

Guidance literature:

With potassium phosphate; C₄₈H₄₇IrNO₄P; In tetrahydrofuran; diethyl ether; at 30 ℃; for 60h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol901151u

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (1S)-1-phenyl-2-propen-1-amine (244092-75-9) → (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate (1169852-67-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃;

DOI:10.1002/anie.201108287

Reference yield:

1-Phenyl-2-propen-1-ol (4393-06-0) → (S)-(9H-fluoren-9-yl)methyl 1-phenylallylcarbamate (1169852-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; chlorobis(cyclooctene)-iridium(I) dimer; aminosulfonic acid; N,N-dimethyl-formamide / 2-methyltetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / dichloromethane; water / 20 °C

With (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; chlorobis(cyclooctene)-iridium(I) dimer; aminosulfonic acid; sodium hydrogencarbonate; N,N-dimethyl-formamide; In 2-methyltetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201108287

upstream raw materials:

fluorenyl carbamate

cinnamyl tert-butyl carbonate

1-Phenyl-2-propen-1-ol

(fluorenylmethoxy)carbonyl chloride

Refernces

• 1、 Weix, Daniel J.,Markovic, Dean,Ueda, Mitsuhiro,Hartwig, John F.. "Direct, intermodular, enantioselective, iridium-catalyzed allylation of carbamates to form carbamate-protected, branched allylic amines". supporting information; experimental part. p. 2944 - 2947. Retrieved 2009/12/05.