(R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 377090-73-8
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 377090-73-8.mol

Synonyms:(R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 4 articles about (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate 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: 64.0%

ethylmagnesium bromide (925-90-6) + 3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate (133464-35-4) → (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate (377090-73-8)

Guidance literature:

With titanium(IV) isopropylate; In diethyl ether; at 20 ℃;

DOI:10.1021/ol016477c

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate (377090-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / BF₃*Et₂O / acetone

2: 64 percent / Ti(i-PrO)4 / diethyl ether / 20 °C

With titanium(IV) isopropylate; boron trifluoride diethyl etherate; In diethyl ether; acetone; 2: Kulinkovich cyclopropanation;

DOI:10.1021/ol016477c

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate (377090-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHCO₃ / H₂O / 3 h / 20 °C

2: 95 percent / BF₃*Et₂O / acetone

3: 64 percent / Ti(i-PrO)4 / diethyl ether / 20 °C

With titanium(IV) isopropylate; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In diethyl ether; water; acetone; 3: Kulinkovich cyclopropanation;

DOI:10.1021/ol016477c

upstream raw materials:

ethylmagnesium bromide

3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

benzyl chloroformate

Downstream raw materials:

(S)-N-carbobenzyloxycleonin

(S)-cleonin

1-(1-(benzyloxycarbonylamino)-2-hydroxyethyl)-1-hydroxycyclopropane