(S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde

Base Information

• Chemical Name: (S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde
• CAS No.: 63126-45-4
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.186
• Hs Code.: 2933990090
• European Community (EC) Number: 622-965-2
• Nikkaji Number: J410.686E
• Wikidata: Q76421710
• Mol file: 63126-45-4.mol

Synonyms:63126-45-4;(S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde;(S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde;(2S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde;(S)-(-)-1-Formyl-2-(methoxymethyl)pyrrolidine;SCHEMBL6855172;JNIOQRWRORXADR-ZETCQYMHSA-N;MFCD00010279;AKOS015851526;AKOS015919241;AS-67350;M1162;2-(Methoxymethyl)-1-pyrrolidinecarbaldehyde #;T72745;1-Pyrrolidinecarboxaldehyde,2-(methoxymethyl)-,(2S)-;(S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde, 98%

Chemical Property of (S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde

Chemical Property:

• Vapor Pressure: 0.00923mmHg at 25°C
• Refractive Index: n20/D 1.4755(lit.)
• Boiling Point: 265.307 °C at 760 mmHg
• PKA: -1.15±0.40(Predicted)
• Flash Point: 100.835 °C
• PSA: 29.54000
• Density: 1.098 g/cm³
• LogP: 0.82740
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 116

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COCC1CCCN1C=O
• Isomeric SMILES: COC[C@@H]1CCCN1C=O
• Uses: Chiral auxiliary reagent for asymmetric C-C coupling.

Technology Process of (S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde

There total 5 articles about (S)-(-)-2-(Methoxymethyl)-1-pyrrolidinecarboxaldehyde 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: 80.0%

(S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine (55456-46-7) + methyl iodide (74-88-4) → (S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde (63126-45-4,121817-71-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; room temperature -> reflux;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + (2S)-2-(methoxymethyl)-1-pyrrolidine (63126-47-6) → (S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde (63126-45-4,121817-71-8)

Guidance literature:

With sodium (phenyltrihydroxyborate); phenylsilane; In diethylene glycol dimethyl ether; at 60 ℃; for 12h; under 1875.19 Torr; Sealed tube; Glovebox; Autoclave;

DOI:10.1039/d0gc01741h

Reference yield:

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → (S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde (63126-45-4,121817-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / 0 °C

2: NaH / tetrahydrofuran / -60 - 20 °C

With sodium hydride; In tetrahydrofuran;

DOI:10.1002/chem.200204660

upstream raw materials:

(S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine

methyl iodide

(S)-1-Pyrrolidin-2-yl-methanol

L-proline

Downstream raw materials:

(R)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-3-methyl-2-phenyl-butan-1-one

(S)-2-Hydroxy-1-((S)-2-methoxymethyl-pyrrolidin-1-yl)-3-methyl-2-phenyl-butan-1-one

2-<(2S)-2-Methoxymethyl-1-pyrrolidinylmethyleneamino>benzenepropanoic acid, methyl ester

α-Ethyl-α-<(2S)-2-methoxymethyl-1-pyrrolidinylmethyleneamino>benzenepropanoic acid, methyl ester

Refernces

• 1、 Denmark, Scott E.,Ares, Jeffrey J.. "Stereoselective alkylations of chiral nitro imine and nitro hydrazone dianions. Synthesis of enantiomerically enriched 3-substituted 1-nitrocyclohexenes". supporting information; scheme or table. p. 9647 - 9656. Retrieved 2009/04/11.
• 2、 Enders, Dieter,Fey, Peter,Kipphardt, Helmut. "(S)-(-)-1-amino-2-methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-amino-2-methoxymethylpyrrolidine (RAMP), versatile chiral auxiliaries". . p. 173 - 173. Retrieved 2017/05/20.