Sodium borohydride → N-Ethoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

HRID 371151Notes

Reaction equation

HRID 371151 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH:7]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:27])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:5])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][C@@H:7]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=1[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13519476N-Ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinone

Product 1

HCID 70413237N-Ethoxycarbonyl-cis-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinolYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a -50° C. solution of 12.1 g (25.1 mmol) of N-ethoxycarbonyl-2-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinone in 90 ml methanol and 90 ml of tetrahydrofuran is added 1.04 g (27.5 mmole) of sodium borohydride. The reaction is stirred 2 hours at -50° C. and then allowed to warm to 25° C. The reaction is quenched by addition to 300 ml saturated sodium chloride and the mixture extracted with ethyl ether (2 liters). The organic extract is washed with 300 ml saturated sodium chloride, dried over magnesium sulfate and the ether evaporated in vacuo. The crude product is purified via column chromatography on 2 kg silica gel eluting in 500 ml fractions with 2% methanol-5% ether-93% dichloromethane to yield (fractions 20-26) 6.04 g (50%) of the title compound as an oil and 3.75 g (31% of a mixture of the title compound and its trans-isomer. Further chromatography yields pure trans-isomer.

Workup

  1. temperatureto warm to 25° C
  2. customThe reaction is quenched by addition to 300 ml saturated sodium chloride
  3. extractionthe mixture extracted with ethyl ether (2 liters)
  4. extractionThe organic extract
  5. washis washed with 300 ml saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customthe ether evaporated in vacuo
  8. customThe crude product is purified via column chromatography on 2 kg silica gel eluting in 500 ml fractions with 2% methanol-5% ether-93% dichloromethane

Sources & evidence

ORD record
ord-dbe06553ebbc476abb9205ff3935aee2
Source dataset
uspto-grants-1985_07
Patent number
US04529732

Reaction notes

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