Technology Process of (R)-2-[(benzyloxycarbonyl)amino]-4-(2,4,6-trimethylphenyl)-1-butanol
There total 4 articles about (R)-2-[(benzyloxycarbonyl)amino]-4-(2,4,6-trimethylphenyl)-1-butanol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
benzyl (4R)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate;
With
9-borabicyclo[3.3.1]nonane dimer;
In
toluene;
at 80 - 85 ℃;
2,4,6-trimethylphenyl bromide;
With
sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetra-(n-butyl)ammonium iodide;
In
toluene;
at 90 ℃;
With
hydrogenchloride;
In
methanol;
for 24h;
Further stages.;
DOI:10.1021/ol005645i
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 8.7 g / NaHCO3 / methanol; ethyl acetate; H2O / biphasic
2.1: 42 percent / Pseudomonas cepecia (Amano PS-30) lipase / CH2Cl2 / 20 °C / Enzymatic reaction
3.1: 100 percent / BF3*Et2O / acetone / -20 - 20 °C
4.1: 9-BBN / toluene / 80 - 85 °C
4.2: aq. NaOH; Pd(PPh3)4; TBAI / toluene / 90 °C
4.3: 68 percent / aq. HCl / methanol / 24 h
With
9-borabicyclo[3.3.1]nonane dimer; Pseudomonas cepecia (Amano PS-30) lipase; boron trifluoride diethyl etherate; sodium hydrogencarbonate;
In
methanol; dichloromethane; water; ethyl acetate; acetone; toluene;
1.1: Acylation / 2.1: Acetylation / 3.1: Condensation / 4.1: hydroboration / 4.2: Suzuki cross-coupling / 4.3: Ring cleavage;
DOI:10.1021/ol005645i
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: 42 percent / Pseudomonas cepecia (Amano PS-30) lipase / CH2Cl2 / 20 °C / Enzymatic reaction
2.1: 100 percent / BF3*Et2O / acetone / -20 - 20 °C
3.1: 9-BBN / toluene / 80 - 85 °C
3.2: aq. NaOH; Pd(PPh3)4; TBAI / toluene / 90 °C
3.3: 68 percent / aq. HCl / methanol / 24 h
With
9-borabicyclo[3.3.1]nonane dimer; Pseudomonas cepecia (Amano PS-30) lipase; boron trifluoride diethyl etherate;
In
dichloromethane; acetone; toluene;
1.1: Acetylation / 2.1: Condensation / 3.1: hydroboration / 3.2: Suzuki cross-coupling / 3.3: Ring cleavage;
DOI:10.1021/ol005645i
