Sodium Hydroxide → HCID 13817560, compound

HRID 649409Notes

Reaction equation

HRID 649409 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:27])[C:22]([O:24]CC)=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([OH:27])[C:22]([OH:24])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13817553Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate

Product 1

HCID 13817560HCID 13817560, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoate (5 g) in methanol (10 ml) is added dropwise a solution of sodium hydroxide (2.6 g) in water (20 ml) at room temperature. After completing addition, the mixture is stirred for 30 minutes, diluted with water (300 ml) and extracted with ethyl ether (50 ml). The aqueous layer is acidified with concentrated hydrochloric acid and extracted with ethyl acetate (200 ml). The extract is washed with water, dried over anhydrous magnesium sulfate and evaporated in vacuo to give 6-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxyhexanoic acid (3.5 g) as a colorless oil.

Workup

  1. additionaddition
  2. extractionextracted with ethyl ether (50 ml)
  3. extractionextracted with ethyl acetate (200 ml)
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f2f02f3a10d04db7be0497e602fadf6e
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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