Sodium borohydride → HCID 58513754, compound

HRID 2362726Notes

Reaction equation

HRID 2362726 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1.[BH4-].[Na+]>CO>[OH:2][CH2:3][CH2:4][O:5][C:6]1([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58513752HCID 58513752, compound

Product 1

HCID 58513754HCID 58513754, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ambient solution of tert-butyl 3-(2-methoxy-2-oxoethoxy)-3-(thiazol-2-yl)pyrrolidine-1-carboxylate (2.05 g, 5.99 mmol) in methanol (29.9 ml) was added NaBH4 (0.680 g, 17.96 mmol). The reaction was stirred for 1 hour and was then quenched by the addition of water (20 mL) and ethyl acetate (20 mL). The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the title compound, which was used in the subsequent step without further purification. MS ESI(+) m/z 314.9 [M+H]+.

Workup

  1. customwas then quenched by the addition of water (20 mL) and ethyl acetate (20 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ethyl acetate (2×20 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae89f94dc63b492886827a92dc0e10be
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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