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281573 Sigma-Aldrich

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

95%

Synonym: SAMP

  • CAS Number 59983-39-0

  • Empirical Formula (Hill Notation) C6H14N2O

  • Molecular Weight 130.19

  •  Beilstein/REAXYS Number 1523794

  •  MDL number MFCD00064485

  •  PubChem Substance ID 24856982

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Heterocyclic Building Blocks, Pyrrolidines More...
assay   95%
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.)
storage temp.   room temp
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

Description

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.

Packaging

1 g in ampule

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
161.6 °F - closed cup
Flash Point(C) 
72 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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