ChemicalBook CAS DataBase List (R)-1-Boc-3-hydroxypyrrolidine

(R)-1-Boc-3-hydroxypyrrolidine synthesis

11synthesis methods

Product Name:(R)-1-Boc-3-hydroxypyrrolidine
CAS Number:109431-87-0
Molecular formula:C9H17NO3
Molecular Weight:187.24

24424-99-5

40499-83-0

83220-73-9

1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine (compound 16) was synthesized by a four-step reaction using di-tert-butyl dicarbonate and 3-hydroxy-pyrrolidine. First, (R)-3-pyrrolidinol (539 mg, 6.19 mmol) was converted to compound 16b to afford a colorless oily product (1.3 g, 100% yield). The spectral data of the product were consistent with the expected structure and in accordance with literature reports (see Kucznierz, R. et al., J. Med. Chem. 1998, 41, 4983-4994). Subsequently, compound 16b was further converted to compound 16c, again as a colorless oil. Next, compound 16c was converted by a two-step reaction to compound 16e, still a colorless oily substance. Finally, compound 16e was converted to the target product compound 16 to give a yellow oily substance.

24424-99-5 Synthesis

24424-99-5
857 suppliers
$13.50/25G

104706-47-0 Synthesis

104706-47-0
376 suppliers
$8.00/5g

109431-87-0
360 suppliers
$5.00/1g

Yield:109431-87-0 99%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 0.12 h;

Steps:

1 Synthesis of tert-butyl (R)-3-hydroxypyrrolidine-1-carboxylate:

To a stirred solution of (R)-pyrrolidin-3-ol hydro chloride (3.0 g, 24.2 mmol) in DCM (30 ml), were added N(Et)₃(10.2 ml, 72.8 mmol) and (Boc)₂0 (6 ml, 26.7 mmol) at 0 °C. The reaction mixture was allowed to stir at room temperature for about 12 hours. After 12 hours of stirring, saturated NH₄C1 was added. The solution was extracted with EtOAc (2x60 mL). The combined organic phases were washed with brine, dried over Na₂S0₄and concentrated under reduced pressure to give the crude product. Purification by flash chromatography with EtOAc-hexane (4: 6) as an eluent to afford the desired product (4.5 g, yield: 99%) as an oil.

References:

WO2017/17630,2017,A1 Location in patent:Page/Page column 36

101385-93-7 Synthesis