Hydrochloric Acid → 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzeneacetic Acid, Methyl Ester Hydrochloride

HRID 2306067Notes

Reaction equation

HRID 2306067 reaction equation
[ClH:1].[OH:2][C:3]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2)=[O:14])[CH2:6][CH2:5]1.[BH4-].[Na+].[OH-].[Na+].Cl>CO>[ClH:1].[OH:2][C:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2)[OH:14])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22471930Methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate hydrochloride

Product 1

HCID 865835134-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenzeneacetic Acid, Methyl Ester HydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

Dissolve 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetic acid, methyl ester hydrochloride (550 mg, 1.00 mmol) in methanol (5 mL) and add sodium borohydride (62.8 mg) in three batches. Stir for 1 hour, add 50% aqueous sodium hydroxide (800 mg) and heat to reflux with stirring. After 3 hours, cool to −10° C., add approximately 1.5 mL of 6N HCl over 10 minutes, filter the solid and wash with ice water (12 mL) such that the final filtrate is pH=5. Dry the resulting solid in vacuo (50°-60° C., 10−1 mm) overnight to give the title compound (515 mg, 94%); mp 165°-180° C.

Workup

  1. temperatureheat
  2. temperatureto reflux
  3. stirringwith stirring
  4. waitAfter 3 hours
  5. filtrationfilter the solid
  6. washwash with ice water (12 mL) such that the final filtrate
  7. customDry the resulting solid in vacuo (50°-60° C., 10−1 mm) overnight

Sources & evidence

ORD record
ord-3adc0db51f2b4b0e8baf26f270015f21
Source dataset
uspto-grants-2002_08
Patent number
US06441179B1

Reaction notes

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