(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

Base Information

Chemical Name:(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin
CAS No.:154429-33-1
Molecular Formula:C₂₀H₃₁N₃O₃Si
Molecular Weight:389.57
Hs Code.:

Synonyms:(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

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Chemical Property of (2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

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Technology Process of (2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

There total 6 articles about (2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin 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: 7.7%

: 151-50-8
potassium cyanide

: 506-87-6,6721-33-1,10361-29-2
ammonium carbonate

: 154343-01-8
(2S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>-4-oxopyrrolidine

: 154429-33-1
(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

: (2S,4R)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

Guidance literature:: In water; N,N-dimethyl-formamide; at 55 - 60 ℃; for 24h;
DOI:10.1016/0957-4166(95)00209-8

Reference yield:

: 33996-30-4
trans-4-hydroxy-L-proline ethyl ester hydrochloride

: 154429-33-1
(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / triethylamine / CH₂Cl₂ / 6 h / Heating

2: 84 percent / LiBH₄ / tetrahydrofuran / 10 h / Ambient temperature

3: 82 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 6 h / -10 °C

4: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

5: 62 percent / dimethylformamide; H₂O / 24 h / 55 - 60 °C

With dmap; lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0957-4166(95)00209-8

Reference yield:

: 107746-25-8
(2S,4R)-1-benzyl-4-hydroxy-2-hydroxymethylpyrrolidine

: 154429-33-1
(2S,4S)-1-benzyl-2-<(tert-butyldimethylsilyloxy)methyl>pyrrolidine-4-spiro-5'-hydantoin

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 6 h / -10 °C

2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 deg C to RT

3: 62 percent / dimethylformamide; H₂O / 24 h / 55 - 60 °C

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0957-4166(95)00209-8