(4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide

Base Information

• Chemical Name: (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide
• CAS No.: 138253-29-9
• Molecular Formula: C₁₈H₂₈N₂O₄
• Molecular Weight: 336.431

Synonyms:(4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide

Chemical Property of (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide

There total 14 articles about (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide 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:

(S)-Pyroglutaminol (17342-08-4) → (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide (138253-29-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 73 percent / NaH / dimethylsulfoxide / 24 h / Ambient temperature

2: DDQ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

3: NaH / tetrahydrofuran / 1 h / Ambient temperature

4: 1) LDA / 1) 2) THF, -78 deg C, 30 min

5: 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / Ambient temperature

6: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

7: p-TsOH*H₂O / 5 h / Ambient temperature

8: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

9: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

10: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

11: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

12: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

13: H₂, AcOH / 5percent Pd/C / methanol; H₂O / 60 h / Ambient temperature

14: p-TsaOH*H₂O / 3 h / Ambient temperature

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)79444-5

Reference yield:

(S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone (152500-26-0) → (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide (138253-29-9)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 1 h / Ambient temperature

2: 1) LDA / 1) 2) THF, -78 deg C, 30 min

3: 30percent aq. H₂O₂ / ethyl acetate / 0.5 h / Ambient temperature

4: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

5: p-TsOH*H₂O / 5 h / Ambient temperature

6: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

7: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

8: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

9: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

10: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

11: H₂, AcOH / 5percent Pd/C / methanol; H₂O / 60 h / Ambient temperature

12: p-TsaOH*H₂O / 3 h / Ambient temperature

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)79444-5

Reference yield:

(S)-1-(4-Methoxy-benzyl)-5-methoxymethyl-1,5-dihydro-pyrrol-2-one (138253-26-6) → (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide (138253-29-9)

Guidance literature:

Multi-step reaction with 9 steps

1: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; toluene / 12.5 h / Ambient temperature

2: p-TsOH*H₂O / 5 h / Ambient temperature

3: ceric ammonium nitrate / acetonitrile; H₂O / 1) 0 deg C, 20 min 2) r.t., 1.5h

4: 4-(N,N-dimethylamino)pyridine / acetonitrile / 10 h / Ambient temperature

5: LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

6: diphenyl phosphorazidate, Et₃N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.

7: TMSOTf / CH₂Cl₂ / 1 h / 0 °C

8: H₂, AcOH / 5percent Pd/C / methanol; H₂O / 60 h / Ambient temperature

9: p-TsaOH*H₂O / 3 h / Ambient temperature

With dmap; lithium hydroxide; osmium(VIII) oxide; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)79444-5

upstream raw materials:

2,2-dimethoxy-propane

(S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone

(S)-1-(4'-methoxybenzyl)-5-methoxymethyl-pyrrolidin-2-one

(S)-1-(4-Methoxy-benzyl)-5-methoxymethyl-1,5-dihydro-pyrrol-2-one

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