[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

Base Information

Chemical Name:[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester
CAS No.:476371-45-6
Molecular Formula:C₁₉H₂₉NO₄
Molecular Weight:335.444
Hs Code.:

Synonyms:[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

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Chemical Property of [2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

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Technology Process of [2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

There total 9 articles about [2-(benzyloxymethyl)-5-methoxycyclopentyl]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: 87.0%

: 67-56-1
methanol

: 476371-56-9
(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

: 476371-45-6
[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h;
DOI:10.1021/ja0258778

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 476371-45-6
[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran; dimethylformamide / 0.25 h / -40 °C

1.2: (+)-IPC₂BH / tetrahydrofuran / 48 h / -10 °C

1.3: 73 percent / aq. H₂O₂; NaOH / 12 h / 20 °C

2.1: 83 percent / pyridine / 12 h / 20 °C

3.1: 77 percent / LAH / diethyl ether / 20 h / Heating

4.1: 85 percent / tert-butyl hydroperoxide; TiCl₄ / CH₂Cl₂; various solvent(s) / 0.25 h / -78 °C

5.1: NaN₃; aq. NH₄Cl / methanol / 15 h / Heating

5.2: methane sulfonyl chloride; pyridine / 2 h / 20 °C

5.3: 84 percent / LAH / tetrahydrofuran / 5 h / 20 °C

6.1: 84 percent / Et₃N / methanol / 2 h / 20 °C

7.1: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -78 °C

With pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; boron trifluoride diethyl etherate; titanium tetrachloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0258778

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 476371-45-6
[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / Et₃N / methanol / 2 h / 20 °C

2: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -78 °C

With boron trifluoride diethyl etherate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ja0258778