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186511

Sigma-Aldrich

(S)-(+)-2-Pyrrolidinemethanol

97%

Sinónimos:

(S)-(+)-2-(Hydroxymethyl)pyrrolidine, L-Prolinol

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About This Item

Fórmula empírica (notación de Hill):
C5H11NO
Número de CAS:
23356-96-9
Peso molecular:
101.15
Beilstein/REAXYS Number:
79843
EC Number:
245-605-2
MDL number:
MFCD00005255
UNSPSC Code:
12352005
PubChem Substance ID:
24851225
NACRES:
NA.22

assay

97%

optical activity

[α]20/D +31°, c = 1 in toluene

refractive index

n20/D 1.4853 (lit.)

bp

74-76 °C/2 mmHg (lit.)

density

1.025 g/mL at 25 °C (lit.)

SMILES string

OC[C@@H]1CCCN1

InChI

1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1

InChI key

HVVNJUAVDAZWCB-YFKPBYRVSA-N

Categorías relacionadas

General description

(S)-(+)-2-Pyrrolidinemethanol, also known as (S)-(+)-prolinol is a chiral building block that is used for the synthesis of chiral organic compounds. It is also used as a chiral auxiliary in asymmetric synthesis and a chiral ligand in asymmetric catalysis.

Application

(S)-(+)-2-Pyrrolidinemethanol can be used as a starting material for the synthesis of (S)-α, α-diaryl-2-pyrrolidinemethanols. It plays an important role in this synthesis by providing chirality to the final product.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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Sigma-Aldrich

139513

1-Methyl-2-pyrrolidine ethanol

Weixu Zhai et al.
Bioorganic & medicinal chemistry letters, 18(18), 5083-5086 (2008-08-30)
The discovery and optimization of a novel series of prolinol-derived GHSR agonists is described. This series emerged from a 11,520-member solid-phase library targeting the GPCR protein superfamily, and the rapid optimization of low micromolar hits into single-digit nanomolar leads can
Katsuhiko Moriyama et al.
The Journal of organic chemistry, 77(21), 9846-9851 (2012-10-12)
The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Brønsted acid worked well as an electrophilic oxidant for this reaction.
Chuan Wang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(37), 11531-11535 (2012-07-28)
Sulfenylated oxindoles: The first asymmetric sulfenylation of N-Boc-protected oxindoles has been developed to provide products containing a tetrasubstituted stereogenic center in high to excellent yields (86-98 %) and, in most cases, excellent enantioselectivities (up to 96 % ee; see scheme).
Ina Mager et al.
Organic letters, 12(7), 1480-1483 (2010-03-06)
A highly efficient approach for the synthesis, application, and recycling of immobilized diarylprolinol silyl ethers was developed. The MeOPEG-supported Jørgensen-Hayashi catalyst provides unchanged reactivity and selectivity as compared to the homogeneous catalyst, as demonstrated for the Michael addition of nitromethane
Tatsuya Urushima et al.
Organic letters, 12(13), 2966-2969 (2010-06-10)
Diarylprolinol was found to be an effective organocatalyst of the direct, enantioselective aldol reaction of commercially available polymeric ethyl glyoxylate, affording gamma-ethoxycarbonyl-beta-hydroxy aldehydes, versatile synthetic intermediates, in good yield with excellent enantioselectivity.
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