3-Substituted 9-Methyl-3,9-Diazabicyclo[3.3.1]nonanes

Steck, Edgar A.; Fletcher, Lynn T.; Brundage, R. Pauline

doi:10.1021/jo01044a019

Cited by 5 publications

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References 2 publications

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“…1.2.3.4-Tetrahydro-6,7-dimethoxy-3-methyl-3-isoquinolinecarboxylic Acid Hydrochloride (10). a-Methyl-(3,4-dimethoxyphenyl)alanine13 (7,12.00 g, 50.3 mmol), 37% formaldehyde solution (40 mL, 532 mmol) and 6 N HC1 (95 mL) were heated at 100 °C for 35 min. The solvent was evaporated and the residue was dried in vacuo overnight to give 15.23 g; single spot by TLC and single peak by GC [derivatized by , -bis(trimethylsilyl)acetamide].…”

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Iminium salts from .alpha.-amino acid decarbonylation. Application to the synthesis of berbines

Dean¹,

Rapoport²

1978

J. Org. Chem.

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confidence: 99%

Iminium salts from .alpha.-amino acid decarbonylation. Application to the synthesis of berbines

Dean¹,

Rapoport²

1978

J. Org. Chem.

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Herstellung von Dihydro‐, Tetrahydro‐ und Hexahydrochelidamsäure‐Derivaten

Hermann

Dreiding

1976

Helvetica Chimica Acta

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(10 nil) and a 35% aqueous formaldehyde solution (7 ml). The mixture was poured into water, inade alkaline with 5~ NaOH and extracted with CHC13. Thc organic layer was dried, evaporated to dryness and the crude base converted t o its naphthalcne-l,5-disulfonate, yielding 6.9 g (69",) of 6b salt, m.p. 250-252". -C25HzsClN05S: C, H, N. ) -2,3,4,5-tctvahyydrn-l H-2-henzazepine (6 d) naphthalene-I, 5-disulfn~zate. Compound 5d was methylated to 6d, which was converted to its naphthalene-l,5-disulfonate as described for 6b, giving 79% of salt, m.p. 253-255". -C Z~H~~N O~S : ,1-[2-(4-Chlornphenyl)ethyZ] -7, S-dimethoxy-2-methyZ-2,3,4,5-tetrahydvn -7 I-I-2-benza:epine (6e) ~taflhtlzale~ze-I, 5-disulfonate. Compound 5 e was methylated to 6e, which was converted l o its naphthalene-l,5-disulfonate as described for 6b, giving 70% of salt, 1n.p. 233-236". -7-[3,4-Dimethoxyhenzyl)-7, 8-dillzethoxy-2-methyl-2,3,4,5-tetvahydro-l H-2-benaazefiine ( 6~) naplzthalene-l,5-disulfnlzate. The aniinc 5c (7.5 g, 21.0 mmol) was dissolved in 25 ml of ethanol, 40 ml of 35% aqueous solution of formaldehyde wcre added, and the solution was refluxcd for 1.5 h.The reaction mixture was then cooled to 0-5" and NaBHa (7,s g, 0.20 mol) was added in small portions. The mixture was allowed to warm up to RT. After addition of a large amount of water, the mixture was extracted with CHC13. The organic layer was dricd, evaporated to dryncss and the residual oil converted to its naphthalene-1,5-disulfonate as for 5b, giving 5.4 g (780/,) of 6c salt, m.p. 233-235'. -C Z~H~~N O~S :C, H, N. 2,3,10,7 7-Tetvametlznxy-5,6,7,7a,8,13-hexahydvo-isoqui~zolo[3,2-a]-Z-henzazepine ( 7 ) .Theaminc 5 c (7.5 g, 21 mmol) was dissolved in Z N HCl (75 ml) and a 35: aqueous formaldehyde solution (40 ml) was added. The mixture was refluxed for 1.5 h, then cooled and madc alkaline with 2 w NaOH. The compound was extracted with CHC13. The organic extract was dried, evaporated to dryness and the residue recrystallized from CHCl3/petrolcum ether, giving 4.7 g (6196) Preparation of dihydro-, tetrahydro-and hexahydro-chelidamic-acid derivatives. -Summavy. Three methods for the preparation of 4-0~0-2,6-piperidine-dicarboxylic acid (3) and derivatives, required as a synthon for betalaine pigments, were explored.

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