Spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one, 4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-, (1'S,2'Z,5'S)-

Base Information

• Chemical Name: Spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one, 4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-, (1'S,2'Z,5'S)-
• CAS No.: 244239-39-2
• Molecular Formula: C24H32N2O2
• Molecular Weight: 380.53
• Mol file: 244239-39-2.mol

Synonyms:

Chemical Property of Spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one, 4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-, (1'S,2'Z,5'S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one, 4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-, (1'S,2'Z,5'S)-

There total 32 articles about Spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one, 4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-, (1'S,2'Z,5'S)- 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: 89.0%

(1S,2Z,5S)-4-methyl-2-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-dispiro[1,4-diazabicyclo[3.2.1]octan-7,1'-cyclohexane-4',2-[1,3]dioxepane] (264271-62-7) → (1'S,2'Z,5'S)-4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one (244239-39-2)

Guidance literature:

With hydrogenchloride; In acetone; at 25 ℃; for 3h;

DOI:10.1021/ol991401q

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-2-(3-oxo-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (752206-18-1) → (1'S,2'Z,5'S)-4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one (244239-39-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: KHMDS / tetrahydrofuran

2.1: 68 percent / KHMDS / diethyl ether; toluene / 20 °C

3.1: aq. K₂OsO₄; NMO / acetone

4.1: aq. NaIO₄ / tetrahydrofuran

5.1: 89 percent / TBAF / tetrahydrofuran

6.1: 87 percent / Et₃N / CH₂Cl₂

7.1: 98 percent / H₂ / Pd/C / ethyl acetate

8.1: 87 percent / NaN₃ / dimethylformamide

9.1: 92 percent / PTSA / benzene

10.1: TFA

11.1: K₂CO₃ / acetonitrile

12.1: H₂ / Pd/C / methanol

13.1: aq. LiOH

14.1: DPPA; Et₃N / dimethylformamide

15.1: 73 percent / NaH / tetrahydrofuran

16.1: LDA / tetrahydrofuran / -78 °C

16.2: MsCl; Et₃N / CH₂Cl₂

16.3: t-BuOK / tetrahydrofuran / 0 °C

17.1: AlH₃ / diethyl ether

18.1: aq. HCl / acetone

With aluminium hydride; hydrogenchloride; lithium hydroxide; potassium osmate(VI); sodium periodate; sodium azide; N-methyl-2-indolinone; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1055/s-2004-829092

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-2-(3-oxo-but-1-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → (1'S,2'Z,5'S)-4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one (244239-39-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 100 percent / H₂ / Pd/C / ethyl acetate

2.1: KHMDS / tetrahydrofuran

3.1: 68 percent / KHMDS / diethyl ether; toluene / 20 °C

4.1: aq. K₂OsO₄; NMO / acetone

5.1: aq. NaIO₄ / tetrahydrofuran

6.1: 89 percent / TBAF / tetrahydrofuran

7.1: 87 percent / Et₃N / CH₂Cl₂

8.1: 98 percent / H₂ / Pd/C / ethyl acetate

9.1: 87 percent / NaN₃ / dimethylformamide

10.1: 92 percent / PTSA / benzene

11.1: TFA

12.1: K₂CO₃ / acetonitrile

13.1: H₂ / Pd/C / methanol

14.1: aq. LiOH

15.1: DPPA; Et₃N / dimethylformamide

16.1: 73 percent / NaH / tetrahydrofuran

17.1: LDA / tetrahydrofuran / -78 °C

17.2: MsCl; Et₃N / CH₂Cl₂

17.3: t-BuOK / tetrahydrofuran / 0 °C

18.1: AlH₃ / diethyl ether

19.1: aq. HCl / acetone

With aluminium hydride; hydrogenchloride; lithium hydroxide; potassium osmate(VI); sodium periodate; sodium azide; N-methyl-2-indolinone; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1055/s-2004-829092

upstream raw materials:

(1S,2Z,5S)-4-methyl-2-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-dispiro[1,4-diazabicyclo[3.2.1]octan-7,1'-cyclohexane-4',2-[1,3]dioxepane]

C₂₆H₃₆N₂O₃

1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate

(3S)-dispiro[3-amino-1-(ethoxycarbonylmethyl)pyrrolidine-5,1'-cyclohexane-4',2''-1,3-dioxolane]