ChemicalBook CAS DataBase List 2-azaadamantane

2-azaadamantane synthesis

7synthesis methods

Product Name:2-azaadamantane
CAS Number:768-41-2
Molecular formula:C9H15N
Molecular Weight:137.22

2-Azatricyclo[3.3.1.13,7]decane, 4-bromo-

1274919-04-8
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768-41-2
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Yield:768-41-2 74%

Reaction Conditions:

Stage #1: C₉H₁₄BrNwith lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 2 h;
Stage #2: with water;sodium hydroxide in tetrahydrofuran;

Steps:

1.v

Step (v): Preparation of compound of formula (6)To a stirred solution of compound of formula (5) (R4 = H) (4.55 grams, 21 mmol) in dry tetrehydrofuran (42 mL) cooled at 0 °C, was added a solution of lithiumaluminium hydride (1M in tetrahydrofuran, 31.5 mL, 31.5 mmol). The reaction mixture was stirred at room temperature for 2 hours before being quenched by adding water ( 1.2 mL), aqueous sodium hydroxide (15%, 1.23 mL) and water (3.5 mL) in sequence. The reaction mixture was filtered through a small pad of celite, the filtrate was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to obtain compound of formula (6) (R4 = H) (2.125 grams). Yield: 74 %.-NMR (CDCI₃): δ 3.19 (bs, 1 H), 2.52 (bs, 1 H), 2.10-1.95 (m, 6H), 1.90-1.85 (m, 2H), 1.82-1.75(m, 4H).Mass (m/z): 138 [M+FT].

References:

WO2011/30349,2011,A1 Location in patent:Page/Page column 21