(2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

Base Information

• Chemical Name: (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine
• CAS No.: 156045-81-7
• Molecular Formula: C₁₈H₃₁NO₂Si
• Molecular Weight: 321.535
• Mol file: 156045-81-7.mol

Synonyms:(2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

Chemical Property of (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

There total 5 articles about (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine 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:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (156045-81-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h

2: 30percent aq. H₂O₂ / ethyl acetate / 0.67 h / 0 - 22 °C

3: 63 percent / t-BuOOH, n-Bu₄NF, K₂CO₃ / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h

4: 79 percent / aluminum amalgam, NaHCO₃ (half sat.) / ethanol; acetone / 2 h

5: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C

6: 1.) BH₃*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et₂O, RT, 6 h

With 1H-imidazole; tert.-butylhydroperoxide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; aluminium amalgam; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)80492-9

Reference yield:

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one (134107-65-6) → (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (156045-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / t-BuOOH, n-Bu₄NF, K₂CO₃ / dimethylformamide; 2,2,4-trimethyl-pentane; tetrahydrofuran / 2 h

2: 79 percent / aluminum amalgam, NaHCO₃ (half sat.) / ethanol; acetone / 2 h

3: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C

4: 1.) BH₃*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et₂O, RT, 6 h

With 1H-imidazole; tert.-butylhydroperoxide; N,N,N,N,-tetramethylethylenediamine; aluminium amalgam; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; 2,2,4-trimethylpentane; ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)80492-9

Reference yield:

bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one (156045-79-3) → (2R,3S)-1-benzyl-3-tert-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine (156045-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / imidazole / dimethylformamide / 6 h / 40 °C

2: 1.) BH₃*SMe, 2.) TMEDA / 1.) THF, 70 deg C, 2 h, 2.) THF, Et₂O, RT, 6 h

With 1H-imidazole; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; In N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)80492-9

upstream raw materials:

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one

(2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one

Downstream raw materials:

(3S,4S)-3-azido-1-benzyl-4-(tert-butyldimethylsilyloxy)piperidine

(2R,3S)-2-(azidomethyl)-1-benzyl-3-(tert-butyldimethylsilyloxy)pyrrolidine

trans-3-hydroxy-L-proline