(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Base Information

Chemical Name:(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one
CAS No.:221301-06-0
Molecular Formula:C₂₀H₂₀N₆O₂
Molecular Weight:376.418
Hs Code.:

Synonyms:(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

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Chemical Property of (1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

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Technology Process of (1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

There total 7 articles about (1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one 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: 73.0%

: 4005-49-6
N-benzoyladenine

: 221300-91-0
(1S,5S,8S)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one

: 221301-06-0
(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Guidance literature:: N-benzoyladenine; With sodium hydride; In N,N-dimethyl-formamide; for 0.25h;

(1S,5S,8S)-8-iodo-2-azabicyclo[3.3.1]nonan-3-one; In N,N-dimethyl-formamide; for 22h; in dark;
DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1

Reference yield:

: 6493-77-2,49543-03-5,68000-20-4,68000-21-5
(S)-(-)-methyl 3-cyclohexene-1-carboxylate

: 221301-06-0
(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

2.1: pyridine / 2 h / 0 °C

3.1: dimethylsulfoxide / 1.5 h / 110 - 120 °C

4.1: 88 percent / H₂O / Raney-Cu / dimethylsulfoxide / 17 h / 95 - 105 °C

5.1: CF₃SO₃SiMe₃; Et₃N / pentane / 1 h / 25 °C

5.2: I₂ / diethyl ether / 3 h

6.1: NaH / dimethylformamide / 0.25 h

6.2: 73 percent / dimethylformamide / 22 h / in dark

With lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; water; sodium hydride; triethylamine; Raney-Cu; In tetrahydrofuran; pyridine; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 1.1: Reduction / 2.1: mesylation / 3.1: Substitution / 4.1: Addition / 5.1: silylation / 5.2: iodolactamization / 6.1: Metallation / 6.2: Alkylation;
DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1

Reference yield:

: 5681-56-1,1679-51-2,5709-99-9,72581-32-9
(S)-4-(Hydroxymethyl)cyclohexene

: 221301-06-0
(1S,5S,8S)-8-(6-benzamido-9H-purin-9-yl)-2-azabicyclo[3.3.1]nonan-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / 2 h / 0 °C

2.1: dimethylsulfoxide / 1.5 h / 110 - 120 °C

3.1: 88 percent / H₂O / Raney-Cu / dimethylsulfoxide / 17 h / 95 - 105 °C

4.1: CF₃SO₃SiMe₃; Et₃N / pentane / 1 h / 25 °C

4.2: I₂ / diethyl ether / 3 h

5.1: NaH / dimethylformamide / 0.25 h

5.2: 73 percent / dimethylformamide / 22 h / in dark

With trimethylsilyl trifluoromethanesulfonate; water; sodium hydride; triethylamine; Raney-Cu; In pyridine; dimethyl sulfoxide; N,N-dimethyl-formamide; pentane; 1.1: mesylation / 2.1: Substitution / 3.1: Addition / 4.1: silylation / 4.2: iodolactamization / 5.1: Metallation / 5.2: Alkylation;
DOI:10.1002/1522-2675(20000607)83:6<1049::AID-HLCA1049>3.0.CO;2-1