tert-butyl 2-acetyl-9-azabicyclo[4.2.1]nonane-9-carboxylate

Base Information

• Chemical Name: tert-butyl 2-acetyl-9-azabicyclo[4.2.1]nonane-9-carboxylate
• CAS No.: 112020-12-9
• Molecular Formula: C₁₅H₂₅NO₃
• Molecular Weight: 267.368
• Mol file: 112020-12-9.mol

Synonyms:9-Azabicyclo[4.2.1]nonane-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, endo- (9CI);9-Azabicyclo[4.2.1]nonane-9-carboxylic acid, 2-acetyl-, 1,1-dimethylethylester, endo-(?à)-

Chemical Property of tert-butyl 2-acetyl-9-azabicyclo[4.2.1]nonane-9-carboxylate

Chemical Property:

• Vapor Pressure: 1.85E-05mmHg at 25°C
• Boiling Point: 363.1°Cat760mmHg
• Flash Point: 173.4°C
• Density: 1.068g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 2-acetyl-9-azabicyclo[4.2.1]nonane-9-carboxylate

There total 25 articles about tert-butyl 2-acetyl-9-azabicyclo[4.2.1]nonane-9-carboxylate 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: 65.0%

(E)- and (Z)-t-butyl 2-(1-methoxyethylidene)-9-azabicyclo<4.2.1>nonane-9-carboxylate (111964-10-4,111964-14-8) → N-Boc dihydroanatoxin-a (90741-49-4,90820-98-7,90821-04-8,90821-05-9,96997-82-9,112020-12-9,112020-13-0)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; for 0.0833333h; Ambient temperature;

Reference yield:

ethyl 2-aminohepta-5,6-dienoate (112009-92-4) → N-Boc dihydroanatoxin-a (90741-49-4,90820-98-7,90821-04-8,90821-05-9,96997-82-9,112020-12-9,112020-13-0)

Guidance literature:

Multi-step reaction with 14 steps

1: CH₂Cl₂

2: 88 percent / AgBF₄ / CH₂Cl₂ / 72 h / Ambient temperature

3: CF₃CO₂H / CH₂Cl₂ / Ambient temperature

4: pyridine / 0 °C

5: 1) B₂H₆, 2) aq. NaOH, 30percent aq. H₂O₂ / 1) THF, 20 deg C, 20 min, 2) 30 min, room temp.

6: 63 percent / tetrahydrofuran / 0.17 h / -10 °C

7: 78 percent / PPh₃, 2 M Br₂ / tetrahydrofuran / a) 0 deg C, 10 min, b) up to room temp.

8: 83 percent / NaH / dimethylsulfoxide / 2 h / 40 °C

9: 92 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / 60 °C

10: 1) LDA / 1) DME, hexane, -78 deg C, 20 min, 2) DME, 5 min

11: NaH / tetrahydrofuran / 14 h / Ambient temperature

12: liquid ammonia, lithium / tetrahydrofuran / 0.05 h / -78 °C

13: methanol / 16 h

14: 65 percent / (CH₃)3SiCl, NaI / acetonitrile / 0.08 h / Ambient temperature

With pyridine; sodium hydroxide; chloro-trimethyl-silane; aluminium amalgam; ammonia; dihydrogen peroxide; bromine; lithium; sodium hydride; triphenylphosphine; trifluoroacetic acid; sodium iodide; diborane; lithium diisopropyl amide; silver tetrafluoroborate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

Reference yield:

ethyl 2-benzylideneaminohepta-5,6-dienoate (112009-90-2) → N-Boc dihydroanatoxin-a (90741-49-4,90820-98-7,90821-04-8,90821-05-9,96997-82-9,112020-12-9,112020-13-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 59 percent / aq. HCl / diethyl ether / 0.67 h / Ambient temperature

2: CH₂Cl₂

3: 88 percent / AgBF₄ / CH₂Cl₂ / 72 h / Ambient temperature

4: CF₃CO₂H / CH₂Cl₂ / Ambient temperature

5: pyridine / 0 °C

6: 1) B₂H₆, 2) aq. NaOH, 30percent aq. H₂O₂ / 1) THF, 20 deg C, 20 min, 2) 30 min, room temp.

7: 63 percent / tetrahydrofuran / 0.17 h / -10 °C

8: 78 percent / PPh₃, 2 M Br₂ / tetrahydrofuran / a) 0 deg C, 10 min, b) up to room temp.

9: 83 percent / NaH / dimethylsulfoxide / 2 h / 40 °C

10: 92 percent / Al-Hg / tetrahydrofuran; H₂O / 3 h / 60 °C

11: 1) LDA / 1) DME, hexane, -78 deg C, 20 min, 2) DME, 5 min

12: NaH / tetrahydrofuran / 14 h / Ambient temperature

13: liquid ammonia, lithium / tetrahydrofuran / 0.05 h / -78 °C

14: methanol / 16 h

15: 65 percent / (CH₃)3SiCl, NaI / acetonitrile / 0.08 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; chloro-trimethyl-silane; aluminium amalgam; ammonia; dihydrogen peroxide; bromine; lithium; sodium hydride; triphenylphosphine; trifluoroacetic acid; sodium iodide; diborane; lithium diisopropyl amide; silver tetrafluoroborate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

(R)-2-Chlorocarbonyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester

(R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester

(1R,2R)- and (1R,2S)-9-(tert-butoxycarbonyl)-2-(methoxycarbonyl)-9-azabicyclo<4.2.1>nonane

C₁₇H₂₇NO₄S₂

Downstream raw materials:

C₂₀H₃₇NO₄Si

(1R,2R,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester

(1R,2R,6R)-9-Aza-bicyclo[4.2.1]nonane-2,9-dicarboxylic acid 9-tert-butyl ester

(1R,2R,6R)-2-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester