(R)-2-Methylpropane-2-sulfinamide
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(R)-2-Methylpropane-2-sulfinamide
structure -
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CAS No:
196929-78-9
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Formula:
C4H11NOS
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Chemical Name:
(R)-2-Methylpropane-2-sulfinamide
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Synonyms:
2-Propanesulfinamide,2-methyl-,[S(R)]-;2-Propanesulfinamide,2-methyl-,(R)-;[S(R)]-2-Methyl-2-propanesulfinamide;(R)-tert-Butanesulfinamide;(R)-(+)-2-Methyl-2-propanesulfinamide;(R)-tert-Butylsulfinamide;(R)-2-Methyl-2-propanesulfinamide;(R)-(+)-tert-Butanesulfinamide;(R)-(+)-tert-Butylsulfinamide;(R)-2-Methylpropane-2-sulfinamide;(R)-(+)-2-Methyl-2-propanesulfinamide;(R)-2-Methylpropan-2-sulfinamide;(R)-tert-Butylsulfinamide;(R)-(+)-tert-Butylsulfinamide;(R)-tert-Butanesulfinamide;(R)-t-Butyl sulfinamide;1461641-92-8;2138272-72-5
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CAS No:
(R)-2-Methylpropane-2-sulfinamide Basic Attributes
121.2
121.20
1806241-263-5
DTXSID40449939
29309090
Characteristics
62.3
0
White, light pink, light yellow to brown Powder
0.903 g/mL at25 °C
101-102 °C @ Solvent: Hexane
220.0±23.0 °C(Predicted)
-17℃
4 ° (C=1, CHCl3)
Soluble in chloroform, methanol, tetrahydrofuran, dichloromethane, dimethyl sulfoxide and most organic solvents.
Keep Cold
4 º (c=1, CHCl3 + amylenes)
Safety Information
UN 2056 3 / PGII
3
11-19-36/37-40-36/37/38
22-24/25-36/37-26-16-36/37/39
Xi,Xn,F
store cold
P210-P280-P301 + P312 + P330-P305 + P351 + P338-P370 + P378-P403 + P235
H225-H302-H319-H335-H351
(R)-2-Methylpropane-2-sulfinamide Use and Manufacturing
in the reaction bottle, adding 150 ml cyclopentyl methyl ether, temperature control -50 °C to -70 °C, access liquid ammonia (30.3 g, 1.78 mole) is added drop 2.5M n-BuLi 396 ml (0.99 mol), during the dropping solution white solid, thermal insulation reaction 0.5 hours. Then drop into the (R)- tert butyl sulfonyl butyl Asia thioester (160.9g, 0 . 83 µM, 96.2percent ee) and 2 - chloro propane (86.4g, 1.1 µM) dissolved in the cyclopentyl methyl ether solution (by the 2nd step the obtained product solution cooled to 0 °C, adding 2 - chloro propane mix), the completion of the dropping, thermal insulation stirring reaction for 1 hour, detecting the end of the reaction. After the reaction solution to dryness under reduced pressure, added 1500 ml methyl tert-butyl ether after, diatomaceous earth filter, steaming and solvent, 140 ml cyclohexane -10 °C to 0 °C beating to obtain fine acicular crystal of (R)- tert butyl Asia sulfonamide 79.5 g, yield 79percent, HPLC: 99.1percent, 99.8percent ee.Chiral sulfinamide 15 was prepared on multi-gram scale using methodology developed by ElIman and co-workers (cf. D. J. Weix, J. A. ElIman, Org. Left. 2003, 5, 1317). Asymmetric mono-oxidation of di-tert-butyl disulfide 22 to give sulfinyl sulfide 23 was achieved usinghydrogen peroxide in acetone at 0 °C with vanadyl bis-acetylacetonate and chiral ligand 24 Ligand was prepared from the corresponding 3, 5-di-tert-butylsalicylaldehyde and (1 S, 2R)-1 - amino-2-indanol (purchased from Sigma Aldrich) according to (Ruck, Rebecca T.; Jacobsen, Eric N. J. Am. Chem. Soc. 2002, 124, 2882). Dropwise addition of hydrogen peroxide over 18 hours and regular monitoring of the reaction by 1H NMR prevented over-oxidation and98percent conversion to the desired mono-oxidised product was achieved. The crude material was then dissolved in THF and added via a dropping funnel to LiNH2 in NH3 at —78 °C. Subsequent 5N2 attack at the sulfinyl results in elimination of tert-butylthiol and inversion of the stereochemistry to provide enantiopure sulfinamide 15 in 48percent yield, after recrystallisation.
Chiral ligand used in pharmaceutical compositions
Computed Properties
Molecular Weight:121.20
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:121.05613515
Monoisotopic Mass:121.05613515
Topological Polar Surface Area:62.3
Heavy Atom Count:7
Complexity:84.2
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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(R)-2-Methylpropane-2-sulfinamide
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