(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

Base Information

Chemical Name:(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester
CAS No.:1025935-52-7
Molecular Formula:C₃₀H₃₁NO₈
Molecular Weight:533.578
Hs Code.:

(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzo<f>quinoline, (R)-(-)-acetylmandelate ester

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Chemical Property of (2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

Chemical Property:

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Technology Process of (2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

There total 11 articles about (2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester 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: 45.0%

: 51019-43-3
(R)-(-)-O-acetylmandelic acid

: 144191-98-0
3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydro-4H-benzoquinoline

: 1025935-52-7
(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

: (2R)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/jo00049a035

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 1025935-52-7
(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1) 4-dimethylaminopyridine, 2) Na₂S₂O₄ / 1) CH₃CN, 18 h, RT, 2) H₂O, EtOAc, 24 h, RT

2: 84 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

3: formic acid / 10percent Pd-C / methanol / 0.5 h / Ambient temperature

4: pyridine / 1 h

5: 75 percent / 4-dimethylaminopyridine, pyridine / 18 h / 5 °C

6: 960 mg / pyridine / 0.5 h / Ambient temperature

7: NaH / tetrahydrofuran / 1 h / Ambient temperature

8: 42 percent / 4-dimethylaminopyridine, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; formic acid; sodium dithionite; sodium hydride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/jo00049a035

Reference yield:

: 24137-17-5
2-benzylamino-[1,4]naphthoquinone

: 1025935-52-7
(2S)-3-acetyl-2-hydroxy-5-<<(tert-butyloxy)carbonyl>oxy>-1,2,3,4-tetrahydrobenzoquinoline, (R)-(-)-acetylmandelate ester

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / tetrahydrofuran; diethyl ether / 1 h / 5 °C

2: 1) 4-dimethylaminopyridine, 2) Na₂S₂O₄ / 1) CH₃CN, 18 h, RT, 2) H₂O, EtOAc, 24 h, RT

3: 84 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

4: formic acid / 10percent Pd-C / methanol / 0.5 h / Ambient temperature

5: pyridine / 1 h

6: 75 percent / 4-dimethylaminopyridine, pyridine / 18 h / 5 °C

7: 960 mg / pyridine / 0.5 h / Ambient temperature

8: NaH / tetrahydrofuran / 1 h / Ambient temperature

9: 42 percent / 4-dimethylaminopyridine, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; formic acid; sodium dithionite; sodium hydride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/jo00049a035