(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

Base Information

Chemical Name:(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde
CAS No.:895138-26-8
Molecular Formula:C₂₀H₂₇NO
Molecular Weight:297.44
Hs Code.:

Synonyms:(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

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Chemical Property of (1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

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Technology Process of (1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

There total 6 articles about (1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde 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: 76.0%

: 895138-24-6
(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbonitrile

: 895138-26-8
(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at 0 - 20 ℃; for 5h;
DOI:10.1021/jm060122n

Reference yield:

: (1S,8S)-(+)-trans-8-[(R)-1-phenylethylamino]cyclooct-4-enol

: 895138-26-8
(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 5 h / 0 °C

1.2: 61 percent / NaBH₄; aq. NaOH / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.1: 85 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 25 °C

3.1: KN[Si(CH₃)3]2 / tetrahydrofuran / 0.17 h / -78 °C

3.2: Et₃B / tetrahydrofuran / -78 °C

3.3: 77 percent / tetrahydrofuran / -78 - 20 °C

4.1: 77 percent / t-BuOK / 1,2-dimethoxy-ethane; methanol / 36 h / 50 °C

5.1: 76 percent / DIBAl-H / CH₂Cl₂ / 5 h / 0 - 20 °C

With oxalyl dichloride; potassium tert-butylate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 2.1: Moffat-Swern oxidation;
DOI:10.1021/jm060122n

Reference yield:

: 895138-20-2
(1S,6S)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one

: 895138-26-8
(1S,6S)-3-allyl-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: KN[Si(CH₃)3]2 / tetrahydrofuran / 0.17 h / -78 °C

1.2: Et₃B / tetrahydrofuran / -78 °C

1.3: 77 percent / tetrahydrofuran / -78 - 20 °C

2.1: 77 percent / t-BuOK / 1,2-dimethoxy-ethane; methanol / 36 h / 50 °C

3.1: 76 percent / DIBAl-H / CH₂Cl₂ / 5 h / 0 - 20 °C

With potassium tert-butylate; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jm060122n