Sodium borohydride → HCID 54139986, compound

HRID 1384311Notes

Reaction equation

HRID 1384311 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:33])[CH:18]([N:20]2[CH2:25][CH2:24][C:23]([OH:32])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)[CH3:19])=[CH:13][C:12]=1[O:34][CH3:35])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]([OH:33])[C@H:18]([N:20]2[CH2:25][CH2:24][C:23]([OH:32])([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:22][CH2:21]2)[CH3:19])=[CH:13][C:12]=1[O:34][CH3:35])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21186636HCID 21186636, compound

Product 1

HCID 54139986HCID 54139986, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of sodium borohydride (0.10 g, 2.64 mmol) and ethanol (5 mL) was stirred 10 min and then 1-(4-benzyloxy-3-methoxyphenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-propan-1-one (1.13 g, 2.54 mmol in 25 mL of ethanol) was added. The reaction was stirred at ambient temperature overnight. The reaction was quenched with water and concentrated at reduced pressure and 40° C. The residue was partitioned between ethyl acetate and water. The phases were separated and the organic layer was washed with water and brine, dried over magnesium sulfate and concentrated to afford 1.16 g of crude product which was a 5:1 mixture of (1R*,2R*) and (1R*,2S*) isomers. The mixture was recrystallized from ethanol/ether/hexane and then recrystallized from ethanol/ether to give 0.47 g (41%) of (1R*,2R*)-1-(4-benzyloxy-3-methoxyphenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-propan-1-ol which had: mp 131-132° C. Analysis calculated for C28H33NO4: C, 75.14; H, 7.43; N, 3.13. Found: C, 75.50; H, 7.33; N, 3.25.

Workup

  1. stirringThe reaction was stirred at ambient temperature overnight
  2. customThe reaction was quenched with water
  3. concentrationconcentrated at reduced pressure and 40° C
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe phases were separated
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto afford 1.16 g of crude product which
  10. additiona 5:1 mixture of (1R*,2R*) and (1R*,2S*) isomers
  11. customThe mixture was recrystallized from ethanol/ether/hexane
  12. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-c271ff5fe5884a538e9b27bf49e05b62
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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