• (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; mp 45–47 °C; ${\left[\alpha \right]}_D^{20}$−14.1 (c 1, CHCl₃) for the (1S,2S,3R,5S) enantiomer.⁷

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 Oxidation of (+)-α-pinene of low enantiomeric excess (∼65% ee) affords 2α-hydroxypinan-3-one, which can be upgraded to a nearly enantiopure compound via crystallization from condensed hexane solutions containing 1% (v/v) of ethylene glycol.⁷

(1)

Purity: recrystallization from ethyl acetate-hexane.

Handling, Storage, and Precautions: hygroscopic crystals. Use in a fume hood.