tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

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Chemical Name:tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate
CAS No.:705293-01-2
Molecular Formula:C₂₁H₃₀FN₃O₅
Molecular Weight:423.485
Hs Code.:

Synonyms:tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

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Chemical Property of tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

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Technology Process of tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

There total 11 articles about tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate 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:

: 705293-00-1
tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-oxopropyl]carbamate

: 705293-01-2
tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

Guidance literature:: With sodium hydroxide; dihydrogen peroxide;
DOI:10.1016/j.bmcl.2007.08.049

Reference yield:

: 690257-98-8
methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate

: 705293-01-2
tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

Guidance literature:: Multi-step reaction with 6 steps

1: methanol; sodium hydroxide; water / 3 h / 20 °C

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / DMF (N,N-dimethyl-formamide) / 16 h / 20 °C

3: potassium permanganate; sodium periodate; potassium carbonate / water; tert-butyl alcohol

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C

5: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 14 h / 90 °C

6: sodium hydroxide; water; dihydrogen peroxide / 1.5 h / 0 °C

With methanol; sodium hydroxide; potassium permanganate; sodium periodate; water; dihydrogen peroxide; potassium acetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water; dimethyl sulfoxide; tert-butyl alcohol;

Reference yield:

: 690258-03-8
(βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-en-1-yl]-L-phenylalanine

: 705293-01-2
tert-butyl [(1S,2S)-3-(dimethylamino)-1-{[(3S)-3-fluoropyrrolidin-1-yl]carbonyl}-2-(4-hydroxyphenyl)-3-oxopropyl]carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / DMF (N,N-dimethyl-formamide) / 16 h / 20 °C

2: potassium permanganate; sodium periodate; potassium carbonate / water; tert-butyl alcohol

3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C

4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 14 h / 90 °C

5: sodium hydroxide; water; dihydrogen peroxide / 1.5 h / 0 °C

With sodium hydroxide; potassium permanganate; sodium periodate; water; dihydrogen peroxide; potassium acetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); water; dimethyl sulfoxide; tert-butyl alcohol;