Lithium borohydride → HCID 67998830, compound

HRID 932200Notes

Reaction equation

HRID 932200 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([C@H:10]2[CH2:15][CH2:14][C:13](=[O:16])[N:12]([C@@H:17]([CH:23]3[CH2:25][CH2:24]3)[C:18](OCC)=[O:19])[C@@H:11]2[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:7]=[CH:8][CH:9]=1>CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:11]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[N:12]([C@@H:17]([CH:23]3[CH2:24][CH2:25]3)[CH2:18][OH:19])[C:13](=[O:16])[CH2:14][CH2:15]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86660736HCID 86660736, compound

Product 1

HCID 67998830HCID 67998830, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of lithium borohydride (2M in THF, 15.46 mL, 30.9 mmol) was added to a solution at 0° C. of (S)-ethyl 2-((2S,3R)-3-(3-chlorophenyl)-2-(4-chlorophenyl)-6-oxopiperidin-1-yl)-2-cyclopropylacetate (Example 249, Step B, 2.3 g, 5.15 mmol) in ether (40 mL). After stirring at ambient temperature for 20 hours, the reaction was quenched with saturated aq. NH4Cl solution and extracted into EtOAc. The organic layer was washed with sat. aq. NaCl solution, dried over sodium sulfate and concentrated to give the title compound as a solid, which was used without further purification.

Workup

  1. customthe reaction was quenched with saturated aq. NH4Cl solution
  2. extractionextracted into EtOAc
  3. washThe organic layer was washed with sat. aq. NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb0ebb9fdf0f42dba6c8ee27a8ba90f8
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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