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Merck
CN

281573

Sigma-Aldrich

(S)-(−)-1-Amino-2-(methoxymethyl)pyrrolidine

95%

Synonym(s):

SAMP

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About This Item

Empirical Formula (Hill Notation):
C6H14N2O
CAS Number:
Molecular Weight:
130.19
Beilstein:
1523794
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay

95%

form

liquid

optical activity

[α]20/D −79°, neat

optical purity

ee: 97% (GLC)

refractive index

n20/D 1.465 (lit.)

bp

42 °C/1.8 mmHg (lit.)

density

0.97 g/mL at 25 °C (lit.)

functional group

ether

SMILES string

COC[C@@H]1CCCN1N

InChI

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

InChI key

BWSIKGOGLDNQBZ-LURJTMIESA-N

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Application

(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine may be used as a chiral auxiliary in the asymmetric synthesis of (S)-2-ethylhexanoic acid and (S)-2-n-propyl-4-pentenoic acid. It can undergo 1,4-addition to (E)-alkenyl-cyclohexyl sulfonates in the presence of zinc bromide to form β-hydrazino-cyclohexyl sulfonates.
Undergoes condensation reactions with carbonyl compounds to produce hydrazones which are useful synthons in highly enantioselective syntheses.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Luca Di Martino et al.
Cellular and molecular gastroenterology and hepatology, 8(3), 427-446 (2019-06-11)
Crohn's disease (CD) is a debilitating inflammatory disorder that affects more than 1.6 million people in North America alone. Members of the tumor necrosis factor superfamily are key regulators of intestinal inflammation; specifically, tumor necrosis factor-like weak inducer of apoptosis
Asymmetric synthesis and enantioselective teratogenicity of 2-n-propyl-4-pentenoic acid (4-en-VPA), an active metabolite of the anticonvulsant drug, valproic acid.
Hauck R-S and Nau H.
Toxicology Letters, 49(1), 41-48 (1989)
Loris R Lopetuso et al.
Inflammatory bowel diseases, 23(3), 392-403 (2017-02-02)
A large body of evidence supports a central role of TLR5 and its natural ligand, flagellin, in Crohn's disease (CD), with the precise mechanism(s) still unresolved. We investigated the role of flagellin/TLR5 in SAMP1/YitFc (SAMP) mice, a spontaneous model of
Ludovica F Buttó et al.
Inflammatory bowel diseases, 25(1), 14-26 (2018-10-09)
TNF-like cytokine 1A (TL1A) and its functional receptor, death-domain-receptor-3 (DR3), are multifunctional mediators of effector and regulatory immunity. We aimed to evaluate the functional role and therapeutic potential of TL1A/DR3 signaling in Crohn's disease-like ileitis. Ileitis-prone SAMP1/YitFc (SAMP) and TNFΔARE/+
Tetrahedron, 49, 1821-1821 (1993)

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