Sodium borohydride → HCID 15479875, compound

HRID 910739Notes

Reaction equation

HRID 910739 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, prepared in accordance with Example 9, in 150 mL of methanol in a 500 mL round bottom flask equipped with a mechanical stirrer is slowly added 0.86 g (0.023 mol) of sodium borohydride, and the reaction is stirred for 2 hr. The methanol is removed in vacuo, and the residue is partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The aqueous layer is extracted with ethyl acetate, the combined organic layers are dried with sodium sulfate, and the ethyl acetate is removed in vacuo to provide crude product. The resultant material is 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. customequipped with a mechanical stirrer
  2. customThe methanol is removed in vacuo
  3. customthe residue is partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer is extracted with ethyl acetate
  5. dry with materialthe combined organic layers are dried with sodium sulfate
  6. customthe ethyl acetate is removed in vacuo
  7. customto provide crude product
  8. customThe resultant material is purified by column chromatography (Davisil grade 633 silica gel
  9. washeluted with a gradient of 2% methanol to methylene chloride to 5% methanol to methylene chloride)

Sources & evidence

ORD record
ord-f586c4aaeb6d478c8d831ae0c6cb89b0
Source dataset
uspto-grants-2011_09
Patent number
US08022220B2

Reaction notes

Loading…