(2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 477293-60-0
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.26300
• Mol file: 477293-60-0.mol

Synonyms:(2S,4S)-tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate;

Chemical Property of (2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 282.5±33.0 °C(Predicted)
• PKA: 14.75±0.40(Predicted)
• PSA: 49.77000
• Density: 1.094±0.06 g/cm3(Predicted)
• LogP: 1.31450
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

(2S,4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylicacidtert-butylester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 9 articles about (2S, 4S)-4-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 99.5%

1,1-dimethylethyl (2S,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate (1123305-80-5) → (2S,4S)-4-hydroxy-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester (477293-60-0,2299231-07-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 10h; Cooling with ice;

Reference yield: 90.0%

(2S,4S)-4-Formyloxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (477293-59-7) → (2S,4S)-4-hydroxy-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester (477293-60-0,2299231-07-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0960-894X(02)00534-6

Reference yield:

1,1-dimethylethyl (2R,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate (924907-62-0) → (2S,4S)-4-hydroxy-2-methylpyrrolidine-1-carboxylic acid tert-butyl ester (477293-60-0,2299231-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium triethylborohydride

2: tetrabutyl ammonium fluoride / tetrahydrofuran

With tetrabutyl ammonium fluoride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1021/ml100212k

upstream raw materials:

(2S,4S)-4-Formyloxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl (2S,4R)-4-hydroxyl-2-methylpyrrolidine-1-carboxylate

1,1-dimethylethyl (2S,4S)-4-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate

4-(tert-butyldimethylsilanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Downstream raw materials:

C₃₅H₄₇NO₃S

2,5-dibromo-N-[(3R,5S)-1-cyano-5-methyl-3-pyrrolidinyl]benzenesulfonamide

1,1-dimethylethyl (2S,4R)-4-{[(2,5-dibromophenyl)sulfonyl]amino}-2-methyl-1-pyrrolidinecarboxylate

1,1-dimethylethyl (2S,4R)-4-amino-2-methyl-1-pyrrolidinecarboxylate

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