ChemicalBook CAS DataBase List BOC-CIS-3-HYDROXY-D-PROLINE

BOC-CIS-3-HYDROXY-D-PROLINE synthesis

8synthesis methods

Product Name:BOC-CIS-3-HYDROXY-D-PROLINE
CAS Number:118492-87-8
Molecular formula:C10H17NO5
Molecular Weight:231.25

24424-99-5 Synthesis

24424-99-5
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118492-86-7
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118492-87-8
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Yield:-

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water at 20; for 2 h;

Steps:

36.A
To (2R,3S)-3-hydroxypyrrolidine-2-carboxylic acid (3.12 g, 23.8 mmol) in dioxane/H₂0 (40 mL/20 mL) was added sodium hydroxide (1.90 g, 47.6 mmol), followed by the dropwise addition of di-tert-butyl dicarbonate (6.23 g, 28.6 mmol) in dioxane (10 mL). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with EtOAc (50 mL) and the phases were separated. The organic layer was washed with 10% NaOH aqueous solution (30 mL). The combined aqueous was acidified with concentrated HC1 until pH=2. The aqueous layer was extracted with DCM. The organic phases were dried (Na₂S0₄) and concentrated to give the crude product (4.8 g).

References:

ARRAY BIOPHARMA INC.;BOYS, Mark Laurence;BRADLEY, Michael;DELISLE, Robert Kirk;HENNINGS, D. David;KENNEDY, April L.;MARMSATER, Fredrik P.;MEDINA, Matthew;MUNSON, Mark C.;RAST, Bryson;RIZZI, James P.;RODRIGUEZ, Martha E.;TOPALOV, George T.;ZHAO, Qian WO2011/79076, 2011, A1 Location in patent:Page/Page column 111