dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

Base Information

Chemical Name:dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane
CAS No.:112917-44-9
Molecular Formula:C₁₆H₂₃NO₃S
Molecular Weight:309.43
Hs Code.:

Synonyms:dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

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Chemical Property of dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

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Technology Process of dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

There total 8 articles about dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane 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:

: 112917-37-0
dl-(1β,2α,3β,5β)-6,6-dimethyl-3-<(phenylsulfonyl)amino>-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 112917-44-9
dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; methanol; at 45 ℃; for 2h;
DOI:10.1021/jm00163a038

Reference yield:

: 112918-30-6
dl-(1α,2α,3α,5α)-3-acetoxy-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 112917-44-9
dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 9 steps

1: 2 N aq. NaOH / methanol; tetrahydrofuran / 3 h / Heating

2: 99 percent / oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -60 °C

3: 75 percent / t-BuOK / dimethylformamide / 8 h / Ambient temperature

4: 60 percent / lithium tri-tert-butoxyaluminiumhydride / tetrahydrofuran / 2.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: NaN₃ / dimethylformamide / 5 h / 75 °C

7: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

8: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

With hydrogenchloride; sodium hydroxide; sodium azide; oxalyl dichloride; potassium tert-butylate; water; dimethyl sulfoxide; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a038

Reference yield:

: 112918-34-0
dl-(1β,2α,3β,5β)-3-azido-6,6-dimethyl-2-<2-(triphenylmethoxy)ethyl>bicyclo<3.1.0>hexane

: 112917-44-9
dl-(1β,2α,3β,5β)-6,6-dimethyl-2-(hydroxyethyl)-3-<(phenylsulfonyl)amino>bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) Ph₃P, 2.) H₂O / 1.) RT, 15 h, 2.) a.) 45 deg C, 2 h, b.) reflux, 1 h

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 1 N aq. HCl / tetrahydrofuran; methanol / 2 h / 45 °C

With hydrogenchloride; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jm00163a038