(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Base Information

Chemical Name:(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane
CAS No.:113033-10-6
Molecular Formula:C₁₇H₂₅NO₃S
Molecular Weight:323.456
Hs Code.:

Synonyms:(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

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Chemical Property of (-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

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Technology Process of (-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

There total 7 articles about (-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane 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: 89.3%

: 113033-09-3
(-)-(1S,2R,3S,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

: 113033-10-6
(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: With methanol; toluene-4-sulfonic acid; for 2h; Ambient temperature;
DOI:10.1248/cpb.37.948

Reference yield:

: 103080-37-1
(1S,2R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-oxo-6,6-dimethylbicyclo<3.1.1>heptane

: 113033-10-6
(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaOMe, 2.) NaBH₄ / 1.) MeOH, 2 h, room t., 2.) MeOH, 18 h

2: 97.7 percent / Et₃N / CH₂Cl₂ / 0.25 h / -20 °C

3: 83.2 percent / NaN₃ / hexamethylphosphoric acid triamide / 2 h / 50 °C

4: LiAlH₄ / diethyl ether / 0 deg C, then reflux, 2 h

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

6: 89.3 percent / MeOH / p-TsOH / 2 h / Ambient temperature

With methanol; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; sodium methylate; triethylamine; toluene-4-sulfonic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1248/cpb.37.948

Reference yield:

: 113033-06-0
(1S,2R,3S,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-hydroxy-6,6-dimethylbicyclo<3.1.1>heptane

: 113033-10-6
(-)-(1S,2R,3S,5R)-2-(2-hydroxyethyl)-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 97.7 percent / Et₃N / CH₂Cl₂ / 0.25 h / -20 °C

2: 83.2 percent / NaN₃ / hexamethylphosphoric acid triamide / 2 h / 50 °C

3: LiAlH₄ / diethyl ether / 0 deg C, then reflux, 2 h

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

5: 89.3 percent / MeOH / p-TsOH / 2 h / Ambient temperature

With methanol; lithium aluminium tetrahydride; sodium azide; triethylamine; toluene-4-sulfonic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1248/cpb.37.948