1H-Azepine-1-carboxylic acid, hexahydro-4-[[(2S)-2-methyl-3-(phenylmethoxy)propyl]amino]-5-(2-meth ylpropoxy)-, 2-(trimethylsilyl)ethyl ester, (4R,5R)-

Base Information

• Chemical Name: 1H-Azepine-1-carboxylic acid, hexahydro-4-[[(2S)-2-methyl-3-(phenylmethoxy)propyl]amino]-5-(2-meth ylpropoxy)-, 2-(trimethylsilyl)ethyl ester, (4R,5R)-
• CAS No.: 392725-01-8
• Molecular Formula: C27H48N2O4Si
• Molecular Weight: 492.775
• Mol file: 392725-01-8.mol

Synonyms:

Chemical Property of 1H-Azepine-1-carboxylic acid, hexahydro-4-[[(2S)-2-methyl-3-(phenylmethoxy)propyl]amino]-5-(2-meth ylpropoxy)-, 2-(trimethylsilyl)ethyl ester, (4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Azepine-1-carboxylic acid, hexahydro-4-[[(2S)-2-methyl-3-(phenylmethoxy)propyl]amino]-5-(2-meth ylpropoxy)-, 2-(trimethylsilyl)ethyl ester, (4R,5R)-

There total 9 articles about 1H-Azepine-1-carboxylic acid, hexahydro-4-[[(2S)-2-methyl-3-(phenylmethoxy)propyl]amino]-5-(2-meth ylpropoxy)-, 2-(trimethylsilyl)ethyl ester, (4R,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: 73.0%

(R)-3-benzyloxy-2-methylpropanal (79026-61-2) + (4R,5R)-4-Amino-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (392724-89-9) → (4R,5R)-4-((S)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (392725-01-8) + (4R,5R)-4-((R)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:

With 4 A molecular sieve; sodium cyanoborohydride; In methanol; acetic acid; at 20 ℃; for 1h; pH=6 - 7;

DOI:10.1021/ol016799g

Reference yield:

N-benzyl-N-(but-3-enyl)-but-3-en-1-amine (132365-02-7) → (4R,5R)-4-((S)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (392725-01-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 59 percent / tetrahydrofuran / -50 - 20 °C

2.1: 90 percent / Grubbs catalyst / CH₂Cl₂ / 24 h / Heating

3.1: 84 percent / m-CPBA / CH₂Cl₂ / 12 h / 0 °C

4.1: chiral Jacobsen (R,R)-Cr(salen) catalyst; TMSN₃ / diethyl ether / 144 h

4.2: 1S-(+)-10-camphorsulfonic acid / methanol / 0.5 h

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 88 percent / TBAI / tetrahydrofuran / 0.5 h / 20 °C

6.1: 98 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

7.1: 4 Angstroem molecular sieves; NaBH₃CN; glacial AcOH / H₂O / 1 h / 20 °C / pH 6 - 7

With trimethylsilylazide; 4 A molecular sieve; chiral Jacobsen (R,R)-Cr(salen) catalyst; hydrogen; sodium hydride; sodium cyanoborohydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(03)00857-3

Reference yield:

2-(trimethylsilyl)-ethoxycarbonyl chloride (20160-60-5) → (4R,5R)-4-((S)-3-Benzyloxy-2-methyl-propylamino)-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (392725-01-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 59 percent / tetrahydrofuran / -50 - 20 °C

2.1: 90 percent / Grubbs catalyst / CH₂Cl₂ / 24 h / Heating

3.1: 84 percent / m-CPBA / CH₂Cl₂ / 12 h / 0 °C

4.1: chiral Jacobsen (R,R)-Cr(salen) catalyst; TMSN₃ / diethyl ether / 144 h

4.2: 1S-(+)-10-camphorsulfonic acid / methanol / 0.5 h

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 88 percent / TBAI / tetrahydrofuran / 0.5 h / 20 °C

6.1: 98 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

7.1: 4 Angstroem molecular sieves; NaBH₃CN; glacial AcOH / H₂O / 1 h / 20 °C / pH 6 - 7

With trimethylsilylazide; 4 A molecular sieve; chiral Jacobsen (R,R)-Cr(salen) catalyst; hydrogen; sodium hydride; sodium cyanoborohydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(03)00857-3

upstream raw materials:

(R)-3-benzyloxy-2-methylpropanal

(4R,5R)-4-Amino-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

2-(trimethylsilyl)-ethoxycarbonyl chloride

N-benzyl-N-(but-3-enyl)-but-3-en-1-amine

Downstream raw materials:

(4R,5R)-4-[((S)-3-Benzyloxy-2-methyl-propyl)-tert-butoxycarbonyl-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

[(4R,5R)-5-Isobutoxy-1-(4-methoxy-benzylcarbamoyl)-azepan-4-yl]-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester

(4R,5R)-4-Isobutoxy-5-((E)-(R)-2-methyl-4-phenyl-but-3-enylamino)-azepane-1-carboxylic acid 4-methoxy-benzylamide

(4R,5R)-4-Isobutoxy-5-[methyl-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-amino]-azepane-1-carboxylic acid 4-methoxy-benzylamide

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