Sodium borohydride → Methyl 4-(4-(4-(Hydroxydiphenylmethyl)-1-piperidinyl)-1-hydroxybutyl)-I+-,I+--dimethylphenylacetate

HRID 910738Notes

Reaction equation

HRID 910738 reaction equation
[OH:1][C:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=2)=[O:13])[CH2:5][CH2:4]1.[BH4-].[Na+]>CO>[OH:1][C:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=2)[OH:13])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 99581012-[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]-2,2-dimethylacetic acid methyl ester

Product 1

HCID 9936344Methyl 4-(4-(4-(Hydroxydiphenylmethyl)-1-piperidinyl)-1-hydroxybutyl)-I+-,I+--dimethylphenylacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 13.5 g of methyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylphenylacetate, prepared in accordance with Example 6, in 250 mL of CH3OH is cooled in an ice CH3OH bath, and 1.8 g of NaBH4 is added in portions. After 1 hr, the mixture is concentrated to a solid. The residue is partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous portion is extracted with EtOAc. The combined organics are washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated in vacuo to afford methyl 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylphenylacetate as a foam.

Workup

  1. temperatureis cooled in an ice CH3OH bath
  2. concentrationthe mixture is concentrated to a solid
  3. customThe residue is partitioned between EtOAc and saturated aqueous NaHCO3
  4. extractionThe aqueous portion is extracted with EtOAc
  5. washThe combined organics are washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46908244bcad4f209cb4c69e1745f3ea
Source dataset
uspto-grants-2011_09
Patent number
US08022220B2

Reaction notes

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