ChemicalBook CAS DataBase List 1-CBZ-3-BOC-AMINO PYRROLIDINE

1-CBZ-3-BOC-AMINO PYRROLIDINE synthesis

5synthesis methods

Product Name:1-CBZ-3-BOC-AMINO PYRROLIDINE
CAS Number:185057-49-2
Molecular formula:C17H24N2O4
Molecular Weight:320.38

99724-19-3 Synthesis

99724-19-3
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185057-49-2
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Yield:185057-49-2 83%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 20; for 24 h;

Steps:

1.A; 4.B; 5.B

[0204] A. 1-Cbz-3-(t-butyloxycarbonyl)aminopyrrolidine [CHEMMOL-00014] [0205] To a solution of 3-(t-butyloxycarbonyl)aminopyrrolidine (5.0 g, 26.8 mmol) in THF (40 mL) was added triethylamine (3.7 mL, 26.8 mmol), followed by the addition of benzyl chloroformate (3.8 mL, 26.8 mmol) slowly. After the reaction mixture was stirred for 24 h at room temperature, the reaction mixture was filtered and solvent removed in vacuo. The residue was dissolved in EtOAc and washed sequentially with 1 N NaHCO3 (100 mL), 1.5 N citric acid (100 mL), and water. The organic layer was dried (MgSO4) and concentrated to dryness in vacuo to give the title compound (7.13 g, 83%). [0206] TLC Rf (C) 0.41; [0207] MS 321 (M+H)+; [0208] Analysis for C17H24N2)4: [0209] Calcd: C, 63.73; H, 7.55; N, 8.74; [0210] Found: C, 64.01, H, 7.39, N, 8.71.; [0304] B. 1-Cbz-3-(t-butyloxycarbonyl)aminopyrrolidine [0305] The title compound was prepared according to the procedure described in Example 1A.; 1-Cbz-(t-butyloxycarbonyl)aminopyrrolidine [0287] The title compound may be prepared according to the procedure described in Example 1A.

References:

US2004/10017,2004,A1 Location in patent:Page/Page column 11; 15; 16