Bicyclo[3.1.1]heptan-2-ol, 3-amino-6,6-dimethyl-, (1R,2S,3R,5R)-

Base Information

• Chemical Name: Bicyclo[3.1.1]heptan-2-ol, 3-amino-6,6-dimethyl-, (1R,2S,3R,5R)-
• CAS No.: 871504-58-4
• Molecular Formula: C9H17NO
• Molecular Weight: 155.24

Synonyms:(1R,2S,3R,5R)-3-Amino-6,6-dimethyl-bicyclo[3.1.1]heptan-2-ol;(1R,2S,3R,5R)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane;(1R,2S,3R,5R)-3-aminoapopinan-2-ol;(1R,2S,3R,5R)-3-amino-6,6-dimethyl-2-hydroxy-bicyclo[3.1.1]heptane;

Chemical Property of Bicyclo[3.1.1]heptan-2-ol, 3-amino-6,6-dimethyl-, (1R,2S,3R,5R)-

Chemical Property:

• PSA: 46.25000
• LogP: 1.44090

Purity/Quality:

Safty Information:

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Technology Process of Bicyclo[3.1.1]heptan-2-ol, 3-amino-6,6-dimethyl-, (1R,2S,3R,5R)-

There total 1 articles about Bicyclo[3.1.1]heptan-2-ol, 3-amino-6,6-dimethyl-, (1R,2S,3R,5R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (1R,2S,3R,5R)-(-)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane (871504-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuOK; n-BuONO

1.2: 76 percent / aq. HCl

2.1: LiAlH₄ / tetrahydrofuran / 24 h / Heating

2.2: 87 percent / aq. NaOH; ethyl acetate / tetrahydrofuran / 4 h / 20 °C

With lithium aluminium tetrahydride; n-Butyl nitrite; potassium tert-butylate; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.09.172

Reference yield: 92.0%

(1R,2S,3R,5R)-(-)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane (871504-58-4) + p-toluenesulfonyl chloride (98-59-9) → N-((1R,2S,3R,5R)-2-Hydroxy-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl)-4-methyl-benzenesulfonamide

Guidance literature:

With triethylamine; In dichloromethane; for 24h;

DOI:10.1016/j.tetlet.2005.09.172

Reference yield: 90.0%

(1R,2S,3R,5R)-(-)-3-amino-6,6-dimethyl-2-hydroxybicyclo[3.1.1]heptane (871504-58-4) + 2-Fluorobenzoyl chloride (393-52-2) → 2-fluoro-N-((1R,2S,3R,5R)-2-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-3-yl)benzamide

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2017.02.003

upstream raw materials:

(1R,5S)-(+)-nopinone

Downstream raw materials:

(1R,2S,3R,5R)-6,6-dimethyl-3-morpholinobicyclo[3.1.1]heptan-2-ol

C₁₈H₂₂N₃O⁽¹⁺⁾*BF₄^(1-)

C₁₈H₁₇F₅N₃O⁽¹⁺⁾*BF₄^(1-)

C₂₁H₂₈N₃O⁽¹⁺⁾*BF₄^(1-)

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