Lithium borohydride → HCID 58573439, compound

HRID 932096Notes

Reaction equation

HRID 932096 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[C:22](OC)=[O:23])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]3[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]3)([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[N:12]([C@@H:21]([CH2:26][CH3:27])[CH2:22][OH:23])[C:11](=[O:28])[C@:10]([CH2:30][CH:31]3[CH2:35][O:34][C:33]([CH3:36])([CH3:37])[O:32]3)([CH3:29])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67999319HCID 67999319, compound

Product 1

HCID 58573439HCID 58573439, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-3-methyl-2-oxopiperidin-1-yl)butanoate prepared above in Step B (734 mg, 1.34 mmol) in ether (12.2 mL) was added lithium borohydride (58.3 mg, 2.68 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 dried (Na2SO4) and concentrated under reduced pressure provided the title compound as a colorless film. The product was used in the next step without further purification.

Workup

  1. customthe reaction was quenched (ice cold 10% citric acid)
  2. extractionextracted (2×EtOAc)
  3. washwashed (sat. aq. NaCl solution)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27fee9bc09f44f19be429aef5860a5fc
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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