Lithium borohydride → HCID 58573507, compound

HRID 1048300Notes

Reaction equation

HRID 1048300 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=3[O:32][CH3:33])[C:13](=[O:34])[C:12]([CH3:39])([C:35](OC)=[O:36])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1>C1COCC1.CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[C@@H:15]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=3[O:32][CH3:33])[C:13](=[O:34])[C:12]([CH2:35][OH:36])([CH3:39])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 58573635HCID 58573635, compound

Product 1

HCID 58573507HCID 58573507, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2M lithium borohydride (1.078 mL, 2.157 mmol) was added to a solution of (5R,6S)-methyl 5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(2,4-dimethoxybenzyl)-3-methyl-2-oxopiperidine-3-carboxylate (Example 88, Step A) (1.17 g, 2.157 mmol) in anhydrous THF (21.57 mL) and anhydrous ether (20 mL) at 0° C. under nitrogen. The reaction was quenched after 58 hours with the addition of sat. aq. NH4Cl and the layers were separated. The aqueous layer was extracted with EtOAc twice and the organics were pooled, washed with sat. aq. NaCl solution, dried (MgSO4), filtered and concentrated in vacuo to provide a colorless oil. Purification using a 80 g SiO2 column and eluting with 35 to 65% EtOAc/hexanes provided the title compound as a ˜30:1 mixture of isomers.

Workup

  1. customThe reaction was quenched after 58 hours with the addition of sat. aq. NH4Cl
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. washwashed with sat. aq. NaCl solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a colorless oil
  9. customPurification
  10. washeluting with 35 to 65% EtOAc/hexanes

Sources & evidence

ORD record
ord-da95dffc25624a8da3acf0c1f5806130
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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