Sodium borohydride → HCID 15479875, compound

HRID 990217Notes

Reaction equation

HRID 990217 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)([OH:33])[CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)=[O:19])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:40][C:37]1[CH:36]=[CH:35][C:34]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)([OH:33])[CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:22][CH:21]=3)[OH:19])[CH2:11][CH2:10]2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11156978HCID 11156978, compound

Product 1

HCID 15479875HCID 15479875, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a −10° C. solution of 6.8 g (0.013 mol) of methyl 4-[4-[4-(bis(4-methylphenyl)hydroxymethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetate in 150 mL of methanol in a 500 mL round bottom flask equipped with a mechanical stirrer was slowly added 0.86 g (0.023 mol) of sodium borohydride, and the reaction was stirred for 2 hr. The methanol was removed in vacuo, and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate, the combined organic layers were dried with sodium sulfate, and the ethyl acetate was removed in vacuo to provide crude product. The resultant material was purified by column chromatography (Davisil grade 633 silica gel, packed in methylene chloride, material applied in chloroform, and eluted with a gradient of 2% methanol to methylene chloride to 5% methanol to methylene chloride) to afford methyl 4-[4-[4-(bis(4-methylphenyl)hydroxymethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetate.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried with sodium sulfate
  5. customthe ethyl acetate was removed in vacuo
  6. customto provide crude product
  7. customThe resultant material was purified by column chromatography (Davisil grade 633 silica gel
  8. washeluted with a gradient of 2% methanol to methylene chloride to 5% methanol to methylene chloride)

Sources & evidence

ORD record
ord-392f8630c96f42d99384432454a752ee
Source dataset
uspto-grants-2002_10
Patent number
US06458958B1

Reaction notes

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