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- W4205682564 abstract "(1R,2R,3S,5R), [168286-10-0] InChI = 1S/C10H19NO/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,12H,4-5,11H2,1-3H3/t6-,7-,8+,10+/m1/s1 InChIKey = LGVDAZQPWJBBGX-ODXREFDESA-N (1S,2S,3R,5S), [69363-09-3] C10H19NO (MW 169.26) InChI = 1S/C10H19NO/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,12H,4-5,11H2,1-3H3/t6-,7-,8+,10+/m0/s1 InChIKey = LGVDAZQPWJBBGX-QHOPCYEYSA-N (reagent used as a chiral source in stereoselective reactions) Alternate Name: ATBH, 3-amino-2-hydroxypinane Physical Data: (1R,2R,3S,5R) mp 48–49.5 °C, [α]D22 +13.1 (c 1.0, CHCl3);1 (1S,2S,3R,5S) mp 45–46.5 °C, [α]D22 −14.3 (c 1.0, CHCl3).1 Solubility: soluble in most organic solvents; e.g. THF, CH2Cl2, CHCl3, EtOAc. Form Supplied in: colorless crystals; not commercially available. Analysis of Reagent Purity: 1H NMR, IR, elemental analysis. Preparative Methods: optically pure (1R,2R,3S,5R)-3-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (ATBH) can be prepared from optically impure (1R,5S)-α-pinene (eq 1).1 Oxidation of (1R,5S)-α-pinene (81% ee) with potassium permanganate and subsequent reaction with hydroxylamine affords the α-hydroxy oxime, which is recrystallized from ethyl ether-hexane to give the enantiomerically enriched product. Reduction of the α-hydroxy oxime with lithium aluminum hydride furnishes (1R,2R,3S,5R)-ATBH in optically pure form. (1S,2S,3R,5S)-ATBH can also be prepared in the same way from (1S,5R)-α-pinene (91% ee).1 (1) Purification: recrystallization from ethyl acetate-hexane. Handling, Storage, and Precautions: hygroscopic crystals. Use in a fume hood." @default.
- W4205682564 created "2022-01-25" @default.
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- W4205682564 date "2002-10-15" @default.
- W4205682564 modified "2023-09-26" @default.
- W4205682564 title "3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol" @default.
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- W4205682564 doi "https://doi.org/10.1002/047084289x.rn00063" @default.
- W4205682564 hasPublicationYear "2002" @default.
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