(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

Base Information

Chemical Name:(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane
CAS No.:128299-81-0
Molecular Formula:C₁₅H₁₉NO₃S
Molecular Weight:293.387
Hs Code.:

Synonyms:(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

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Technology Process of (3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

There total 14 articles about (3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>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:

: 98-09-9
benzenesulfonyl chloride

: 128299-81-0
(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 1) 14.7percent aq.NaOCl, 2 N NaOH, 2) 5 N NaOH / 1) a) r.t., 1 h, b) r.t. to 100 deg C, 30 min., c) reflux, 15 min., 2) a) r.t., 30 min., b) 40 min.

2: 95.4 percent / NaBH₄, I₂ / 1,2-dimethoxy-ethane / 0.5 h / 10 °C

3: 1) oxalyl chloride, DMSO 2) Et₃N / 1) CH₂Cl₂, -55 deg C, 15 min., 2) -55 deg C to r.t., 45 min.

4: 1) KO-t-Bu / 1) THF, 0 deg C, 30 min., 2) 0 deg C, 30 min.

5: formic acid / 1 h / Ambient temperature

With sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; formic acid; oxalyl dichloride; potassium tert-butylate; iodine; dimethyl sulfoxide; triethylamine; In 1,2-dimethoxyethane;
DOI:10.1021/jo00006a030

Reference yield:

: 128217-59-4
(3'R,4'R,5'S,6'S)-5'-(2-Hydroxyethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

: 128299-81-0
(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; trimethylamine; In dichloromethane; at -78 ℃; for 0.75h;
DOI:10.1021/jo00304a019

Reference yield:

: 128217-54-9
5-benzyloxy-2-(E)-pentenocarboxylic acid

: 128299-81-0
(3'R,4'R,5'S,6'S)-5'-(Formylmethyl)-4'-benzenesulfonamidobicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 7 steps

2: Et₂AlCl / CH₂Cl₂ / 5 h / -78 °C

3: 87.9 percent / 30percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 10 h / 3 °C

5: Et₃N / CH₂Cl₂ / 1.)0 deg C, 30 min., 2.)r.t., 1,5 h

6: 84.4 percent / 6N HCl, H₂ / 10percent Pd / C / aq. ethanol / 18 h / 2068.6 - 2327.2 Torr

7: oxalyl chloride - DMSO, trimethylamine / CH₂Cl₂ / 0.75 h / -78 °C

With hydrogenchloride; lithium hydroxide; oxalyl dichloride; hydrogen; dihydrogen peroxide; diethylaluminium chloride; dimethyl sulfoxide; triethylamine; trimethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo00304a019