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

HRID 2244769Notes

Reaction equation

HRID 2244769 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 in 250 mL of CH3OH is cooled in an ice CH3OH bath, and 1.8 g of NaBH4 was added in portions. After 1 hr, the mixture was concentrated to a solid. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous portion was extracted with EtOAc. The combined organics were 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. concentrationthe mixture was concentrated to a solid
  2. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. extractionThe aqueous portion was extracted with EtOAc
  4. washThe combined organics were washed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b19b351af20a432c8955c9c914156499
Source dataset
uspto-grants-2010_03
Patent number
US07678915B2

Reaction notes

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