BOC-CIS-3-HYDROXY-D-PROLINE synthesis
- Product Name:BOC-CIS-3-HYDROXY-D-PROLINE
- CAS Number:118492-87-8
- Molecular formula:C10H17NO5
- Molecular Weight:231.25
24424-99-5
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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
118449-01-7
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1000210-73-0
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