(R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone

Base Information

• Chemical Name: (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone
• CAS No.: 109242-47-9
• Molecular Formula: C₂₀H₂₈NO₃P
• Molecular Weight: 361.421

Synonyms:(R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone

Chemical Property of (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone

Chemical Property:

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Technology Process of (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone

There total 3 articles about (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone 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: 75.0%

cyclopent-2-enone (930-30-3) + (2S,4R,5R)-2-Allyl-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 2-oxide (109361-23-1) → (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone (109242-47-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ja00250a047

Reference yield:

(1R,2R)-norephedrine hydrochloride (53643-20-2) → (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone (109242-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaOAc-HOAc-NaBH₄, 2.) LiAlH₄ / 1.) H₂O, 0 deg C, 2.) ether, 25 deg C, 30 min

2: 45 percent / Et₃N / toluene / 1.) -40 deg C, 1 h, 2.) 25 deg C, 12 h

3: 75 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; sodium acetate; acetic acid; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja00250a047

Reference yield:

(1R,2R)-(-)-α-(1-isopropylaminoethyl)benzyl alcohol (109361-28-6) → (R)-3-[(E)-3-((2S,4R,5R)-3-Isopropyl-4-methyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclopentanone (109242-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / Et₃N / toluene / 1.) -40 deg C, 1 h, 2.) 25 deg C, 12 h

2: 75 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja00250a047

upstream raw materials:

cyclopent-2-enone

(2S,4R,5R)-2-Allyl-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 2-oxide

(1R,2R)-norephedrine hydrochloride

(1R,2R)-(-)-α-(1-isopropylaminoethyl)benzyl alcohol

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