L-Prolinol, (S)-(+)-2-(Hydroxymethyl)pyrrolidine
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:
Beilstein/REAXYS Number:
EC Number:
MDL number:
PubChem Substance ID:
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Quality Level



optical activity

[α]20/D +31°, c = 1 in toluene

refractive index

n20/D 1.4853 (lit.)


74-76 °C/2 mmHg (lit.)


1.025 g/mL at 25 °C (lit.)

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InChI key


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Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

WGK Germany


Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Janine Cossy
Chemical record (New York, N.Y.), 5(2), 70-80 (2005-04-13)
The synthesis of optically active substituted piperidines has been achieved by using four different methodologies. The first one is an intramolecular nucleophilic displacement of activated alcohol moieties that was used to build up the piperidine ring of (-)-prosophylline and (-)-slaframine...
Magnus Rueping et al.
Organic & biomolecular chemistry, 10(30), 6201-6210 (2012-05-16)
A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael...
Yuko Kawanami et al.
The Journal of organic chemistry, 74(20), 7908-7921 (2009-09-19)
The photochirogenesis of 2-anthracenecarboxylic acid (AC) complexed to a hydrogen-bonding template (TKS159) was investigated to obtain mechanistic information on how chirogenesis is achieved for the dimerization of AC. Complexation of AC to TKS159 leads to the shielding of one of...
Patrick Bolze et al.
Organic letters, 10(17), 3753-3756 (2008-07-29)
A simple organocatalytic approach to highly attractive chiral building blocks is presented. By the reaction of beta-ketoesters with alpha,beta-unsaturated aldehydes using a chiral TMS-protected prolinol as the catalyst, optically active 5-(trialkylsilyl)cyclohex-2-enones are formed in good yields and with 98-99% ee....
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.

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