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752800

Sigma-Aldrich

[(S,S)-Teth-TsDpen RuCl]

Synonym(s):

stereoisomer of Chloro[N-[(1S,2S)-1,2-diphenyl-2-[(R)-[3-(η6-phenyl)propyl]amino-κN]ethyl]-4-methylbenzenesulfonamidato-κN]ruthenium

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About This Item

Empirical Formula (Hill Notation):
C30H31ClN2O2RuS
CAS Number:
851051-43-9
Molecular Weight:
620.17
UNSPSC Code:
12352103
PubChem Substance ID:
329766311
NACRES:
NA.22

form

solid

Quality Level

100

optical activity

[α]22/D +339°, c = 0.5% in chloroform

reaction suitability

core: ruthenium
reagent type: catalyst

mp

260-268 °C

storage temp.

2-8°C

SMILES string

Cc1ccc(cc1)S(=O)(=O)N2[C@H]([C@@H]([N@@H](CCCc3ccccc3)[Ru]2Cl)c4ccccc4)c5ccccc5

InChI

1S/C30H31N2O2S.ClH.Ru/c1-24-19-21-28(22-20-24)35(33,34)32-30(27-17-9-4-10-18-27)29(26-15-7-3-8-16-26)31-23-11-14-25-12-5-2-6-13-25;;/h2-10,12-13,15-22,29-31H,11,14,23H2,1H3;1H;/q-1;;+2/p-1/t29-,30-;;/m0../s1

InChI key

MDABGVLQRDDWLY-ARDORAJISA-M

Application

[(S,S)-Teth-TsDpen RuCl] is a catalyst for the asymmetric hydrogenation of ketones. It can be used as a catalyst:
  • In the reduction of a ketone intermediate for the synthesis of esketamine.
  • In asymmetric hydrogenation of acetylenic ketones.
  • For the preparation of (3S,6S)-1,8-diphenylocta-1,7-diyne-3,6-diol starting from 1,8-diphenylocta-1,7-diyne-3,6-dione.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR9975
MKCS0064
MKCS4034
MKCQ5723
MKCQ4458

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Asymmetric transfer hydrogenation of functionalized acetylenic ketones
Fang Z and Wills M
The Journal of Organic Chemistry, 78(17), 8594-8605 (2013)
Aidan M Hayes et al.
Journal of the American Chemical Society, 127(20), 7318-7319 (2005-05-19)
Ruthenium dimer 6 (readily available in two steps from TsDPEN) is converted directly to monomeric asymmetric transfer hydrogenation catalyst 3 in situ under the conditions employed for ketone reduction. Catalyst 3 is a significantly more active catalyst for this application
Iron cyclopentadienone complexes derived from C 2-symmetric bis-propargylic alcohols; preparation and applications to catalysis
Hodgkinson R, et al.
Dalton Transactions, 45(9), 3992-4005 (2016)
Enantioselective Syntheses of (S)-Ketamine and (S)-Norketamine
Chen C and Lu X
Organic Letters, 21(16), 6575-6578 (2019)

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