ChemicalBook CAS DataBase List (3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE

(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE synthesis

8synthesis methods

Product Name:(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
CAS Number:131878-23-4
Molecular formula:C16H24N2O2
Molecular Weight:276.37

24424-99-5 Synthesis

24424-99-5
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114715-39-8
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(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE

131878-23-4
102 suppliers
$8.00/1g

Yield: 65.2%

Reaction Conditions:

Stage #1:(R)-1-benzyl-3-aminopyrrolidine with sodium hydrogencarbonate in water;acetonitrile at 20; for 0.166667 h;
Stage #2:di-tert-butyl dicarbonate in water;acetonitrile at 20;

Steps:

1 6.2.1 Synthesis of tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate, 2aa
Sodium bicarbonate (5.92 g, 70.5 mmol) in 118 mL of deionized water was added to (3R)-(+)-benzylaminopyrrolidine 1a (5.00 g, 28.4 mmol) solution in 118 mL of acetonitrile and the mixture was stirred at room temperature for 10 min. Di-tert-butyl dicarbonate (6.22 g, 28.5 mmol) was then added and the mixture was stirred at room temperature overnight. After the reaction, the solution was concentrated under reduced pressure and the residue was extracted with dichloromethane three times. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with flash column chromatography (methanol: dichloromethane = 2:98). Removing the solvent in vacuo provided 4.24 g of tert-butyl (R)-(1-benzylpyrrolidin-3-yl)carbamate (65.2% yield). ¹H NMR (400 MHz, CDCl₃) δ 7.36-7.26 (m, 5H), 4.86 (bs, 1H), 4.18 (bs, 1H), 3.61 (s, 2H), 2.79 (bs, 1H), 2.65-2.61 (m, 1H), 2.54 (d, J = 8.0 Hz, 1H), 2.34-2.25 (m, 2H), 1.61-1.51 (m, 1H), 1.46 (s, 9H). [α]_D +2.5° (c 0.620, CHCl₃).

References:

Chough, Chieyeon;Joung, Misuk;Lee, Sunmin;Lee, Jaemin;Kim, Jong Hoon;Kim, B. Moon [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 8,p. 1495 - 1510]

100-52-7 Synthesis