methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate
CAS No.:206994-54-9
Molecular Formula:C₂₈H₂₉NO₅
Molecular Weight:459.542
Hs Code.:

Synonyms:methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

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Chemical Property of methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

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Technology Process of methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

There total 3 articles about methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate 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: 76.0%

: 206994-52-7
methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

: 74-88-4
methyl iodide

: 1236783-60-0
methyl (S)-4-methoxy-3-(methoxymethoxy)-1-(9-phenyl-9H-fluoren-9-yl)-2,5-dihydro-1H-pyrrole-2-carboxylate

: 206994-54-9
methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

Guidance literature:: methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hexamethylsilazane; In toluene; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In toluene; at -78 ℃; for 2h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo1009239

Reference yield:

: 160882-77-9
(2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

: 206994-54-9
methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

2: 1.) n-BuLi, HMPA, 3.) NaBH₄ / 1.) THF, hexane, -78 deg C, 1.2 h, 2.) -78 deg C to 0 deg C, 4.5 h, 3.) THF, MeOH, -78 deg C, 4 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; In N,N-dimethyl-formamide;
DOI:10.1021/jo980078m

Reference yield:

: 206994-52-7
methyl (2S,3S)-3-(methoxymethoxy)-4-oxo-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

: 74-88-4
methyl iodide

: 206994-54-9
methyl (2S,3S,4R)-4-hydroxy-3-(methoxymethoxy)-3-methyl-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2-carboxylate

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 1.2 h, 2.) -78 deg C to 0 deg C, 4.5 h, 3.) THF, MeOH, -78 deg C, 4 h;
DOI:10.1021/jo980078m