Lithium borohydride → HCID 67999428, compound

HRID 1048216Notes

Reaction equation

HRID 1048216 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][C@H:8]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C@@H:11]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:10]([C@@H:28]([CH2:34][CH3:35])[C:29](OCC)=[O:30])[C:9]1=[O:36])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>CCOCC>[Cl:20][C:16]1[CH:15]=[C:14]([C@@H:12]2[C@@H:11]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:10]([C@@H:28]([CH2:34][CH3:35])[CH2:29][OH:30])[C:9](=[O:36])[C@@H:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:37])[CH2:13]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86660716HCID 86660716, compound

Product 1

HCID 67999428HCID 67999428, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-ethyl 2-((3R,5R,6S)-3-(2-tert-butoxy-2-oxoethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate (1.94 g, 3.54 mmol, Example 21, Step A) in Et2O (35.4 mL) was added 90% lithium borohydride (0.154 g, 7.07 mmol) at 0° C. After being stirred at 0° C. for 30 min, the reaction was quenched (ice cold 10% citric acid), extracted (2×EtOAc) and washed (sat. aq. NaCl solution). The combined organic layers were washed with sat. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure. Purification by chromatography on silica gel (50% to 100% EtOAc/Hexanes, gradient elution) provided the title compound.

Workup

  1. customthe reaction was quenched (ice cold 10% citric acid)
  2. extractionextracted (2×EtOAc)
  3. washwashed (sat. aq. NaCl solution)
  4. washThe combined organic layers were washed with sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customPurification by chromatography on silica gel (50% to 100% EtOAc/Hexanes, gradient elution)

Sources & evidence

ORD record
ord-84ce028cf29243419a3d32d73dcb6b21
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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