(S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate

Base Information

• Chemical Name: (S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate
• CAS No.: 761460-04-2
• Molecular Formula: C₁₃H₂₃NO₅
• Molecular Weight: 273.329
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90460275
• Wikidata: Q82284272
• Mol file: 761460-04-2.mol

Synonyms:(S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate;761460-04-2;tert-butyl (3S)-3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate;SCHEMBL13093519;DTXSID90460275;(S)-tert-Butyl3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate;MFCD23701548;AKOS016008889;CS-W000780;DS-4646;W17763;A865538;TERT-BUTYL (S)-3-(2-ETHOXY-2-OXOETHYL)MORPHOLINE-4-CARBOXYLATE

Chemical Property of (S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate

Chemical Property:

• Boiling Point: 348.1±27.0 °C(Predicted)
• PKA: -2.31±0.40(Predicted)
• PSA: 65.07000
• Density: 1.094±0.06 g/cm3(Predicted)
• LogP: 1.51340
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 273.15762283
• Heavy Atom Count: 19
• Complexity: 324

Purity/Quality:

99% ^*data from raw suppliers

(S)-tert-Butyl3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1COCCN1C(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)C[C@H]1COCCN1C(=O)OC(C)(C)C

Technology Process of (S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate

There total 6 articles about (S)-tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-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:

3-[1-Ethoxycarbonyl-meth-(E)-ylidene]-morpholine-4-carboxylic acid tert-butyl ester → (3S)-4-tert-butoxycarbonyl-3-carbethoxymethylmorpholine (761460-04-2) + 3-ethoxycarbonylmethyl-morpholine-4-carboxylic acid tert-butyl ester

Guidance literature:

With hydrogen bromide; hydrogen; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); [(COD)Ir(Cl)]; In dichloromethane; at 20 ℃; for 24h; under 37503 Torr; Further Variations:; Reagents; Solvents; Pressures; Product distribution;

DOI:10.1055/s-2004-835659

Reference yield:

tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate (761460-02-0) → (3R)-4-tert-butoxycarbonyl-3-carboxymethylmorpholine (761460-03-1,839710-38-2) + (3S)-4-tert-butoxycarbonyl-3-carbethoxymethylmorpholine (761460-04-2)

Guidance literature:

With Burkholderia cepacia lipase; hydrogenchloride; In tetrahydrofuran; phosphate buffer; at 25 ℃; for 10h; pH=7;

DOI:10.1016/j.tetasy.2004.09.022

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S)-4-tert-butoxycarbonyl-3-carbethoxymethylmorpholine (761460-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetyl chloride / 36 h

1.2: Et₃N / CH₂Cl₂ / 24 h / 20 - 40 °C

2.1: aq. HCl; Burkholderia cepacia lipase / tetrahydrofuran; aq. phosphate buffer / 10 h / 25 °C / pH 7

With Burkholderia cepacia lipase; hydrogenchloride; acetyl chloride; In tetrahydrofuran; phosphate buffer;

DOI:10.1016/j.tetasy.2004.09.022

upstream raw materials:

tert-Butyl 3-(2-ethoxy-2-oxoethyl)morpholine-4-carboxylate

di-tert-butyl dicarbonate

ethyl 2-(morpholin-3-yl)acetate

2-(morpholin-3-yl)acetic acid

Downstream raw materials:

(5S)-N-tert-butoxycarbonyl-5-(2-hydroxyethyl)morpholine

Refernces

• 1、 Pousset, Cyrille,Callens, Roland,Marinetti, Angela,Larchevêque, Marc. "An efficient synthesis of chiral cyclic β-amino acids via asymmetric hydrogenation". . p. 2766 - 2770. Retrieved 2007/10/03.