(R)-(-)-3-Quinuclidinol synthesis

6synthesis methods

Product Name:(R)-(-)-3-Quinuclidinol
CAS Number:25333-42-0
Molecular formula:C7H13NO
Molecular Weight:127.18

1193-65-3 Synthesis

1193-65-3
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$19.00/5g

25333-42-0
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$60.00/1g

Yield:25333-42-0 93%

Reaction Conditions:

with D-glucose in aq. phosphate buffer; pH=8 at 37; for 30 h;Concentration;Temperature;pH-value;Time;

Steps:

2.7. Preparation of 3-quinuclidinol
General procedure: For Nocardia sp. WY1202, 3-quinuclidinone hydrochloride (1.6 g, 9.9 mmol) and glucose (2.7 g) were added into suspension of resting cells (8 g, wet weight) in 100 ml of phosphate buffer (100 mM, pH 8.0). The resulting mixture was incubated at 30 °C and 200 rpm for 48 h. For R. erythropolis WY1406, 3-quinuclidinone hydrochloride (1.0 g, 6.2 mmol) and glucose (3.3 g) were added into suspension of resting cells (8.5 g, wet weight) in 125 ml of phosphate buffer (100 mM, pH 8.0). The resulting mixture was incubated at 37 °C and 200 rpm for 30 h. After centrifugation at 7875×g for 20 min, the bacterial cells were washed with water and centrifuged again. The supernatantswere combined and alkalified by addition of K₂CO₃ (pH 12). The mixture was evaporated under vacuum, then CH₂Cl₂ was added to the residue. The mixture was stirred and filtrated. The filtrate was concentrated under vacuum to give crude product. Then acetone was added to the crude product, stirred and concentrated under vacuum to yield 3-quinuclidinol as white powder. 1.17 g(9.20 mmol) (R)-3-quinuclidinol (93% yield) and 0.73 g (5.74 mmol) (S)-3-quinuclidinol (92% yield) were obtained. The ee value were all >99%. 1H NMR: (600 MHz, CDCl₃) δ_ppm: 1.33 (m, 1H), 1.43 (m, 1H),1.65 (m, 1H), 1.80 (m, 1H), 1.90 (m, 1H), 2.25 (br, 1H), 2.60 (m, 1H),2.65 (m, 1H), 2.74 (m, 2H), 2.89 (m, 1H), 3.12 (m, 1H), 3.85 (m, 1H).

References:

Wang, Yu;Li, Jianjiong;Wu, Qiaqing;Zhu, Dunming [Journal of Molecular Catalysis B: Enzymatic,2013,vol. 88,p. 14 - 19]

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