Product Name

  • Name

    Aliskiren inter-8

  • EINECS
  • CAS No. 172900-83-3
  • Article Data5
  • CAS DataBase
  • Density 1.046 g/cm3
  • Solubility
  • Melting Point
  • Formula C24H39NO6
  • Boiling Point 554.43 °C at 760 mmHg
  • Molecular Weight 437.577
  • Flash Point 289.109 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 172900-83-3 (Aliskiren inter-8)
  • Hazard Symbols
  • Synonyms Carbamicacid, [(1S,3S)-1-formyl-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methylpentyl]-,1,1-dimethylethyl ester (9CI);Carbamic acid,[1-formyl-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methylpentyl]-,1,1-dimethylethyl ester, [S-(R*,R*)]-;
  • PSA 83.09000
  • LogP 4.79840

Synthetic route

(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol
172900-82-2

(2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexan-1-ol

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 0 - 20℃; for 1h;100%
With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine at 0 - 20℃; for 1h;100%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane Swern oxidation;89%
methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
656241-21-3

methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -75℃; for 0.833333h;
Multi-step reaction with 2 steps
1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
2: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine
866030-33-3

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HCl / acetonitrile
2: Et3N
3: NaBH4 / ethanol
4: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
isovanillin
621-59-0

isovanillin

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 98 percent / K2CO3 / acetonitrile
2: NaBH4 / ethanol
3: PBr3 / CH2Cl2
4: 76 percent / LiHMDS / tetrahydrofuran
5: 81 percent / LiOH; H2O2
6: 95 percent / LAH / tetrahydrofuran
7: 97 percent / PPh3; NBS / CH2Cl2
8: 68 percent / n-BuLi
9: HCl / acetonitrile
10: Et3N
11: NaBH4 / ethanol
12: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 11 steps
1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 24 h / 20 °C
2.1: sodium tetrahydroborate; ethanol / 20 °C
3.1: pyridine; phosphorus tribromide / diethyl ether / 3 h / 20 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
4.2: 20 °C / Cooling with acetone-dry ice
5.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
6.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
7.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
8.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
8.2: 0 °C
9.1: dichloromethane / 14 h / 20 °C
10.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
11.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one
145589-03-3

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
5: 68 percent / n-BuLi
6: HCl / acetonitrile
7: Et3N
8: NaBH4 / ethanol
9: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 8 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
1.2: 20 °C / Cooling with acetone-dry ice
2.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
4.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
5.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
5.2: 0 °C
6.1: dichloromethane / 14 h / 20 °C
7.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
8.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
4-methoxy-3-(3-methoxypropoxy)benzaldehyde
172900-75-3

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: NaBH4 / ethanol
2: PBr3 / CH2Cl2
3: 76 percent / LiHMDS / tetrahydrofuran
4: 81 percent / LiOH; H2O2
5: 95 percent / LAH / tetrahydrofuran
6: 97 percent / PPh3; NBS / CH2Cl2
7: 68 percent / n-BuLi
8: HCl / acetonitrile
9: Et3N
10: NaBH4 / ethanol
11: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 10 steps
1.1: sodium tetrahydroborate; ethanol / 20 °C
2.1: pyridine; phosphorus tribromide / diethyl ether / 3 h / 20 °C
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
3.2: 20 °C / Cooling with acetone-dry ice
4.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
6.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
7.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
7.2: 0 °C
8.1: dichloromethane / 14 h / 20 °C
9.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
10.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol
172900-70-8

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 97 percent / PPh3; NBS / CH2Cl2
2: 68 percent / n-BuLi
3: HCl / acetonitrile
4: Et3N
5: NaBH4 / ethanol
6: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 6 steps
1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
2.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
3.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
3.2: 0 °C
4.1: dichloromethane / 14 h / 20 °C
5.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid
172900-71-9

(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 95 percent / LAH / tetrahydrofuran
2: 97 percent / PPh3; NBS / CH2Cl2
3: 68 percent / n-BuLi
4: HCl / acetonitrile
5: Et3N
6: NaBH4 / ethanol
7: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene
172900-73-1

4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
5: 68 percent / n-BuLi
6: HCl / acetonitrile
7: Et3N
8: NaBH4 / ethanol
9: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 8 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
1.2: 20 °C / Cooling with acetone-dry ice
2.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
4.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
5.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
5.2: 0 °C
6.1: dichloromethane / 14 h / 20 °C
7.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
8.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol
172900-74-2

[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: PBr3 / CH2Cl2
2: 76 percent / LiHMDS / tetrahydrofuran
3: 81 percent / LiOH; H2O2
4: 95 percent / LAH / tetrahydrofuran
5: 97 percent / PPh3; NBS / CH2Cl2
6: 68 percent / n-BuLi
7: HCl / acetonitrile
8: Et3N
9: NaBH4 / ethanol
10: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 9 steps
1.1: pyridine; phosphorus tribromide / diethyl ether / 3 h / 20 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
2.2: 20 °C / Cooling with acetone-dry ice
3.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
5.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
6.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
6.2: 0 °C
7.1: dichloromethane / 14 h / 20 °C
8.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
9.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 68 percent / n-BuLi
2: HCl / acetonitrile
3: Et3N
4: NaBH4 / ethanol
5: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester
172900-99-1

(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ethyl ester

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N
2: NaBH4 / ethanol
3: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
172900-76-4

ethyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / ethanol
2: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one
172900-72-0

(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 81 percent / LiOH; H2O2
2: 95 percent / LAH / tetrahydrofuran
3: 97 percent / PPh3; NBS / CH2Cl2
4: 68 percent / n-BuLi
5: HCl / acetonitrile
6: Et3N
7: NaBH4 / ethanol
8: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
View Scheme
Multi-step reaction with 7 steps
1.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
3.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
4.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
4.2: 0 °C
5.1: dichloromethane / 14 h / 20 °C
6.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
7.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(R)-­4-(2-(iodomethyl)­-3-­methylbutyl)-­1-­methoxy-2­-(3-­methoxypropoxy)benzene
900811-38-3

(R)-­4-(2-(iodomethyl)­-3-­methylbutyl)-­1-­methoxy-2­-(3-­methoxypropoxy)benzene

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
1.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
2.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
2.2: 0 °C
3.1: dichloromethane / 14 h / 20 °C
4.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
5.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
isopentanoyl chloride
108-12-3

isopentanoyl chloride

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Cooling with acetone-dry ice
1.2: 2.33 h / 0 °C / Cooling with acetone-dry ice
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / Cooling with acetone-dry ice
2.2: 20 °C / Cooling with acetone-dry ice
3.1: lithium borohydride; water / diethyl ether / 0.67 h / 0 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 3 h
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / Cooling with acetone-dry ice
5.2: 16.17 h / -78 °C / Cooling with acetone-dry ice
6.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
6.2: 0 °C
7.1: dichloromethane / 14 h / 20 °C
8.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
9.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
methyl (2S,4S)-2-amino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
656241-36-0

methyl (2S,4S)-2-amino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 14 h / 20 °C
2: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
3: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
656241-17-7

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; water / acetonitrile / 3 h / 20 °C
1.2: 0 °C
2.1: dichloromethane / 14 h / 20 °C
3.1: lithium borohydride / tetrahydrofuran / 15 h / 20 °C
4.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 1 h / 0 - 20 °C
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

(2S)-(benzyloxymethyl)-3-methyl-butyl bromide
172901-00-7

(2S)-(benzyloxymethyl)-3-methyl-butyl bromide

(1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

(1S,4S,2'S)-(4-benzyloxymethyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (2S)-(benzyloxymethyl)-3-methyl-butyl bromide With magnesium; ethylene dibromide In tetrahydrofuran at 55℃; for 0.333333h;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran at 20℃; for 3h; Further stages.;		53%
With magnesium
Stage #1: (2S)-(benzyloxymethyl)-3-methyl-butyl bromide With magnesium; ethylene dibromide In tetrahydrofuran at 55℃; for 0.833333h;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran at 5 - 20℃; for 3h;
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl (1S,3S)-3-(3-(3-methoxypropoxy)-4-methoxybenzyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate
861901-07-7

tert-butyl (1S,3S)-3-(3-(3-methoxypropoxy)-4-methoxybenzyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate

Conditions
ConditionsYield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 20℃; for 1h;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h;		46%
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

tert-butyl (1S,3S)-3-(3-(3-methoxypropoxy)-4-methoxybenzyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate
861901-07-7

tert-butyl (1S,3S)-3-(3-(3-methoxypropoxy)-4-methoxybenzyl)-4-methyl-1-((R)-oxiran-2-yl)pentylcarbamate

Conditions
ConditionsYield
Stage #1: trimethylsulfoxonium iodide With sodium hydride In dimethyl sulfoxide at 20℃; for 1h;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Product distribution / selectivity;		46%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate at 20℃;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 2h;
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

methacrylic acid N-(butyl)amide
28384-61-4

methacrylic acid N-(butyl)amide

A

(1S,2S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3'-methyl-butyl}-pent-4-enyl)-carbamic acid tert-butyl ester

(1S,2S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3'-methyl-butyl}-pent-4-enyl)-carbamic acid tert-butyl ester

B

(1S,2R,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3'-methyl-butyl}-pent-4-enyl)-carbamic acid tert-butyl ester

(1S,2R,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3'-methyl-butyl}-pent-4-enyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: methacrylic acid N-(butyl)amide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h;
Stage #2: With triisopropoxytitanium(IV) chloride In tetrahydrofuran; hexane at -78℃; for 0.916667h;
Stage #3: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran; hexane at -78℃; for 1.5h; Further stages.;		A 76 g
B 188 g
...Expand
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl (1S,3S)-1-((2R,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentylcarbamate

tert-butyl (1S,3S)-1-((2R,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Mg
2: H2 / Pd(OH)2/C
3: TPAP; NMMO
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate
866030-35-5

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
3: 38 percent / TPAP; NMMO
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

((1S,2R,4S)-2-Hydroxy-4-hydroxymethyl-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester
866030-40-2

((1S,2R,4S)-2-Hydroxy-4-hydroxymethyl-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mg
2: H2 / Pd(OH)2/C
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

((1S,2S,4S)-2-hydroxy-4-hydroxymethyl-1-((S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl)-5-methyl-hexyl)-carbamic acid tert-butyl ester
866030-34-4

((1S,2S,4S)-2-hydroxy-4-hydroxymethyl-1-((S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl)-5-methyl-hexyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

4-epi-aliskiren

4-epi-aliskiren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Mg
2: H2 / Pd(OH)2/C
3: TPAP; NMMO
4: 2-hydroxypyridine; Et3N
5: TMSCl; phenol / CH2Cl2
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

((1S,2R,4S)-4-(2-Carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

((1S,2R,4S)-4-(2-Carbamoyl-2-methyl-propylcarbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Mg
2: H2 / Pd(OH)2/C
3: TPAP; NMMO
4: 2-hydroxypyridine; Et3N
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate
173338-07-3

tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
3: 38 percent / TPAP; NMMO
4: 65 percent / 2-hydroxypyridine; Et3N
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide
173334-57-1

(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Mg
2: 23 percent / H2 / Pd(OH)2/C
3: 38 percent / TPAP; NMMO
4: 65 percent / 2-hydroxypyridine; Et3N
5: TMSCl; phenol / CH2Cl2
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

(4S,5S,7S)-5-tert-Butoxycarbonylamino-4-hydroxy-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnon-2-ynoic acid ethyl ester
878276-68-7

(4S,5S,7S)-5-tert-Butoxycarbonylamino-4-hydroxy-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnon-2-ynoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: propynoic acid ethyl ester With lithium diisopropyl amide In tetrahydrofuran for 0.5h;
Stage #2: (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester In tetrahydrofuran at -78℃; for 1h;
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl {1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate
861901-11-3

tert-butyl {1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 1 h / 20 °C
1.2: 1 h / 20 °C
2.1: ammonia; water / methanol / 20 °C
View Scheme
(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester
172900-83-3

(1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester

tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-methoxy-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

tert-butyl (2S,3S,5S)-5-(3-(3-methoxypropoxy)-4-methoxybenzyl)-1-(1,1-dioxo-4-methoxy-1,2,5-thiadiazol-3-ylamino)-2-hydroxy-6-methylheptan-3-ylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 1 h / 20 °C
1.2: 1 h / 20 °C
2.1: acetonitrile / 0.33 h / 90 °C / Microwave
View Scheme

tert-Butyl [(1S,3S)-3-[3-(3-methoxypropoxy)-4-methoxybenzyl]-1-formyl-4-methylpentyl]carbamate Chemical Properties

Product Name: tert-Butyl [(1S,3S)-3-[3-(3-methoxypropoxy)-4-methoxybenzyl]-1-formyl-4-methylpentyl]carbamate (CAS NO.172900-83-3)

Molecular Formula: C24H39NO6
Molecular Weight: 437.57g/mol
Mol File: 172900-83-3.mol
Boiling point: 554.43 °C at 760 mmHg
Flash Point: 289.109 °C
Density: 1.046 g/cm3
Surface Tension: 35.657 dyne/cm
Enthalpy of Vaporization: 83.55 kJ/mol  

tert-Butyl [(1S,3S)-3-[3-(3-methoxypropoxy)-4-methoxybenzyl]-1-formyl-4-methylpentyl]carbamate Specification

 tert-Butyl [(1S,3S)-3-[3-(3-methoxypropoxy)-4-methoxybenzyl]-1-formyl-4-methylpentyl]carbamate , its CAS NO. is 172900-83-3, the synonyms are Aliskiren inter-8 ; (1S,3S)-{1-formyl-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid tert-butyl ester .

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