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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

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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Yuanxia Qin et al.
Journal of agricultural and food chemistry, 67(11), 3168-3178 (2019-02-26)
In this study we report a secretory protein that was purified from Serratia marcescens strain S3 isolated from soil from the tobacco rhizosphere. Subsequent mass spectrometry and annotation characterized the protein as secretory alkaline metalloprotease (SAMP). SAMP plays a crucial
Synlett, 897-897 (1992)
Synthesis, 725-725 (1993)
Asymmetric Synthesis of ?-Amino-cyclohexyl Sulfonates via azaMichael Addition
Enders D and Wallert S.
Synlett, 2002(02), 0304-0306 (2002)
Luca Di Martino et al.
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