Hydrochloric Acid → HCID 563051, compound

HRID 657173Notes

Reaction equation

HRID 657173 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH:4]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C.[BH4-].[Na+].Cl>C(OCC)(=O)C=C>[OH:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:5][CH:4]1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 563051HCID 563051, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8821Ethyl AcrylateSolvent

Procedure

To a solution of ethyl 4-oxo-1-(phenylmethyl)-3-piperidinecarboxylate hydrochloride (56.2 g, 190 mmol) in methanol (11) was added triethylamine (31.8 mL, 230 mmol) and the mixture stirred at room temperature for 10 min. Sodium borohydride (24.0 g, 630 mmol) was then added portionwise with ice cooling, and the reaction was then stirred at room temperature for 4.5 h. 5N HCl solution (200 mL) was added and the mixture was evaporated. The aqueous residue was basified with aqueous sodium bicarbonate and the extracted several times with a 9:1 dichloromethane:methanol mixture. The extracts were dried and evaporated to give the product (44.3 g, 89%) as a mixture of cis and trans isomers.

Workup

  1. stirringthe reaction was then stirred at room temperature for 4.5 h
  2. customthe mixture was evaporated
  3. customThe extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-e8599f111815424cae5d691dff0c2982
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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