Lithium borohydride → HCID 67998830, compound

HRID 1048514Notes

Reaction equation

HRID 1048514 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-3522198b8ea547d9bf697d5773562836
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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