Ethanol → tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propenyl)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

HRID 1858613Notes

Reaction equation

HRID 1858613 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]2[O:37][CH2:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=2)=[CH:20][CH:19]=1)=O)C.C(O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O>[OH:13][CH2:14][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH:25]2[O:37][CH2:38][C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 53757216tert-butyl (3RS,4RS)-4-[4-(2-ethoxycarbonyl-vinyl)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Product 1

HCID 53719730tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propenyl)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylateYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-50 °C

Procedure

5 ml (5 mmol) of a solution of diisobutylaluminium hydride (DIBAH) (1M in hexane) were added dropwise at -50° C. to a solution of 698 mg (1.35 mmol) of tert-butyl (3RS,4RS)-4-[4-(2-ethoxycarbonyl-vinyl)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate in 15 ml of toluene and the mixture was stirred at -50° C. for 30 minutes. Subsequently, the reaction mixture was treated dropwise at -50° C. with 10 ml of ethanol and warmed to room temperature. For the working-up, the reaction mixture was treated with 20 ml of water and 20 ml of saturated potassium sodium tartrate solution while cooling with ice and thereafter extracted three times with 50 ml of ethyl acetate each time. The organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. The crude product was chromatographed on silica gel using a 6:4 mixture of hexane and ethyl acetate as the eluent. There were obtained 354 mg (55% of theory) of tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propenyl)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 474 (M+H)+.

Workup

  1. temperaturewarmed to room temperature
  2. temperaturewhile cooling with ice
  3. extractionextracted three times with 50 ml of ethyl acetate each time
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customThe crude product was chromatographed on silica gel using
  7. additiona 6:4 mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d83ee34ce47d41ddaa1a4351553d59b1
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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