59983-39-0

Basic information

• Product Name: (S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE
• Synonyms: 2-(Methoxymethyl)-1-pyrrolidinamine;(S)-(-)-1-AMINO-2-(METHOXYMETHYL)-PYRROL IDINE, 95% (97% EE/GLC);1-Pyrrolidinamine, 2-(methoxymethyl)-, (2S)-;1-Pyrrolidinamine,2-(methoxymethyl)-,(2S)-(9CI);(S)-(-)-2-(Methoxymethyl)-1-pyrrolidinamine;(2S)-1-Amino-2-(methoxymethyl)pyrrolidine;(2S)-1-Amino-2α-(methoxymethyl)pyrrolidine;(2S)-2α-(Methoxymethyl)-1-pyrrolidinamine
• CAS NO: 59983-39-0
• Molecular Formula: C₆H₁₄N₂O
• Molecular Weight: 130.19
• Product Categories: PYRROLIDINE;chiral;Asymmetric Synthesis;Synthetic Organic Chemistry;Chiral Compound;Aromatics;Chiral Reagents;Heterocycles
• Mol File: 59983-39-0.mol

Chemical Properties

• Boiling Point: 42 °C1.8 mm Hg(lit.)
• Flash Point: 162 °F
• Appearance: /
• Density: 0.97 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.761mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Storage Temp.: 2-8°C
• PKA: 7.93±0.40(Predicted)
• BRN: 1523794
• CAS DataBase Reference: (S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE(59983-39-0)
• EPA Substance Registry System: (S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE(59983-39-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 59983-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its ability to undergo condensation reactions with carbonyl compounds to produce hydrazones.
Used in Organic Synthesis:
(S)-(-)-1-AMINO-2-(METHOXYMETHYL)PYRROLIDINE is used as a chiral building block for the highly enantioselective synthesis of complex organic molecules, as the produced hydrazones serve as valuable synthons in organic chemistry.

InChI:InChI=1/C6H14N2O/c1-9-5-6-3-2-4-8(6)7/h6H,2-5,7H2,1H3/t6-/m0/s1

Upstream product

• 60096-50-6 (S)-N-Nitroso-O-methylprolinol 
• 147-85-3 L-proline 
• 89999-42-8 (S)-2-methoxymethyl-1-(3-phenylpropylidenamino)pyrrolidine 
• 107496-25-3 [(R)-2-(tert-Butyl-dimethyl-silanyl)-3-phenyl-prop-(Z)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 108439-26-5 (3S,4S)-4-{[(E)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-methyl}-3,5-diphenyl-pentanoic acid methyl ester 
• 95312-82-6 (S)-(-)-1-carbamoyl-2-methoxymethylpyrrolidine 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 55456-46-7 (S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine 
• 63126-45-4 (S)-2-(methoxymethyl)pyrrolidine-1-carbaldehyde 

Downstream Products

• 65651-54-9 [1,2-Dimethyl-prop-(Z)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 89999-42-8 (S)-2-methoxymethyl-1-(3-phenylpropylidenamino)pyrrolidine 
• 107381-30-6 hydrocinnamaldehyde SAMP-hydrazone 
• 107538-62-5 (+)-(S)-1-(1,2-diphenyl-ethylideneamino)-2-methoxymethyl pyrrolidine 
• 91658-36-5 (2S)-2-(methoxymethyl)-N-methylidenepyrrolidin-1-amine 
• 72170-87-7 (+)-(2S)-N-[cyclohex-2-en-1-yliden]-2-(methoxymethyl)pyrrolidin-1-amine 
• 72170-91-3 (-)-(S)-2-methoxymethyl-2-(1-pentylideneamino)pyrrolidine 
• 91658-08-1 (+)-(S)-2-methoxymethyl-1-(1-propylbutylideneamino)-pyrrolidine 
• 89393-52-2 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[1-methyl-hex-(Z)-ylidene]-amine 
• 91658-09-2 (+)-(S)-1-(1-n-butylpentylideneamino)-2-methoxymethyl-pyrrolidine 
• 90080-03-8 ((S)-2-methoxymethyl-pyrrolidin-1-yl)-octylidene-amine 
• 72170-92-4 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-oct-(E)-ylidene-amine 
• 101305-95-7 5-Chloro-pentanoic acid ((S)-2-methoxymethyl-pyrrolidin-1-yl)-amide 
• 131906-26-8 (S)-<<1'-(trifluoromethyl)ethylidene>amino>-2-(methoxymethyl)pyrrolidine 

Relevant articles and documents

Stereoselective alkylations of chiral nitro imine and nitro hydrazone dianions. Synthesis of enantiomerically enriched 3-substituted 1-nitrocyclohexenes

(Chemical Equation Presented) Dianions of chiral nitro imines (generated by a combination of LDA and s-BuLi) underwent diastereoselective alkylation with methyl, butyl, isopropyl, allyl, and methallyl iodides. In contrast to the behavior of simple metalloenamines, the most selective auxiliary contained no coordinating groups but did possess a large steric difference between the two substituents. The yield and selectivity of the alkylations were improved by the addition of HMPA or DMPU. The use of (S)-1-naphthylethylamine as the auxiliary afforded the R absolute configuration of the alkylation products. This stereochemical outcome could be rationalized by simple steric approach controlled alkylation in a conformationally fixed, internally coordinated dianion. A SAMP nitro hydrazone gave poorer yields and selectivities.

ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-/RAMP-HYDRAZONES ANTI-DIASTEREO- AND ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED 5-OXO-ALKANOATES

An efficient and highly anti-diastereo-(de=90-100percent) and enantioselective (ee=92-100percent) synthesis of 3,4-disubstituted 5-oxo-alkanoates 3 in good overall chemical yields is described.The procedure involves the asymmetric Michael addition of aldehydes or ketones to enoates via their lithiated SAMP-/RAMP-hydrazones.Both enantiomers are accessible at will.

ASYMMETRIC SYNTHESES VIA METALATED CHIRAL HYDRAZONESOVERALL ENANTIOSELECTIVE α-ALKYLATION OF ACYCLIC KETONES

A general method is described, which allows the overall enantioselective α-alkylation of acyclic ketones in good overall yields (44-86percent, 4 steps) and enantioselectivities ranging routinely from >94percent ee up to virtually complete asymmetric induction (99.5percent ee).The acyclic ketones are transformed to their corresponding "SAMP-hydrazones" (S)-2 by reaction with the enantiomerically pure hydrazine (S)-1-amino-2-methoxymethyl-pyrrolidine , readily available from (S)-proline.Metalation to form chiral azaenolates (S)-3 of ECCZCN-configuration and then alkylation to product hydrazones 4, followed by hydrazone cleavage via acidic hydrolysis of methiodides 9 in a two phase system or ozonolysis, leads to α-substituted, enantiomerically enriched, acyclic ketones 5.In special cases, where a phenyl group is directly attached to the newly generated center of chirality (5n,o,p), only low enantiomeric excesses are observed. 17 Examples, including first applications in natural product synthesis (cf 5a,b,e, and h) are summarized.