Water → HCID 71009538, compound

HRID 1527426Notes

Reaction equation

HRID 1527426 reaction equation
C([BH-](CC)CC)C.[Li+].[C:9]([O:13][C:14]([N:16]1[C@H:21]([C:22](=[O:33])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=2[F:32])[CH2:20][C@:19]2([CH2:34]OS(C)(=O)=O)[C@H:17]1[CH2:18]2)=[O:15])([CH3:12])([CH3:11])[CH3:10].O>C1COCC1>[C:9]([O:13][C:14]([N:16]1[C@H:21]([C:22](=[O:33])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=2[F:32])[CH2:20][C@:19]2([CH3:34])[C@H:17]1[CH2:18]2)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 23664628LithiumtriethylborohydrideHCID 86673855HCID 86673855, compound

Product 1

HCID 71009538HCID 71009538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium triethylborohydride (1N in THF, 2.06 mL, 2.06 mmol) was added at 0° C. to a solution of (1R,3S,5S)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-5-methanesulfonyloxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (385 mg, 0.67 mmol) in THF (6.8 mL) under argon atmosphere. The solution was stirred 10 min at 0° C., then poured into cold water and extracted with EtOAc (×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 75:25). TLC, Rf (c-hexane/EtOAc 1:1)=0.55; MS (UPLC/MS): 383.3/385.3 [M+H]+, 427.5/429.4 [M+HCOO]−; tR (HPLC conditions f): 2.24 min.

Workup

  1. extractionextracted with EtOAc (×2)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 75:25)
  6. custom2.24 min.

Sources & evidence

ORD record
ord-80c73c9df7064cff88ebbab1ecf7457f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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