Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

52057

Sigma-Aldrich

(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidinediol

≥97.0% (sum of enantiomers, HPLC)

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H15NO2
CAS Number:
90365-74-5
Molecular Weight:
193.24
Beilstein/REAXYS Number:
4992458
MDL number:
MFCD01073893
UNSPSC Code:
12352005
PubChem Substance ID:
57651357
NACRES:
NA.22

assay

≥97.0% (sum of enantiomers, HPLC)

form

solid

optical activity

[α]20/D +33.6±3°, c = 1.05% in methanol

mp

94-100 °C

SMILES string

O[C@H]1CN(C[C@@H]1O)Cc2ccccc2

InChI

1S/C11H15NO2/c13-10-7-12(8-11(10)14)6-9-4-2-1-3-5-9/h1-5,10-11,13-14H,6-8H2/t10-,11-/m0/s1

InChI key

QJRIUWQPJVPYSO-QWRGUYRKSA-N

Application

(3S,4S)-(+)-1-Benzyl-3,4-pyrrolidinediol can be used:
  • As a building block for the preparation of novel chiral crown ethers.[1]
  • As an intermediate in the synthesis of (3R,4R)1-benzyl-4-fluoropyrrolidin-3- amine.[2]
  • As an intermediate in the preparation of 3-hydroxy-4-pyrrolidinyl analogs of nucleobases.[3]

Other Notes

Building blocks for novel chiral crown ethers[4][5]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBB9827V
BCBB9827
1384074
1364544
1312781

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases
Rejman D, et al.
Tetrahedron, 63(5), 1243-1253 (2007)
H. Watanabe et al.
Reactive functional Polymers, 37, 101-101 (1998)
Enantiospecific Synthesis of (3R,4R)-1-Benzyl-4-fluoropyrrolidin-3-amine Utilizing a Burgess-Type Transformation
Widlicka DW, et al.
Organic Process Research & Development, 23(9), 1970-1978 (2019)
S. Cicchi et al.
Journal of the Chemical Society. Perkin Transactions 1, 1367-1367 (1998)
Synthesis and phase-transfer catalytic activity of novel chiral crown ethers immobilized onto polystyrene supports
Watanabe H, et al.
Reactive and Functional Polymers, 37(1-3), 101-109 (1998)

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service