Hexane → tert-Butyl 3-ethynylpiperidine-1-carboxylate

HRID 1172731Notes

Reaction equation

HRID 1172731 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=[C:15](Br)Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CCCCCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[CH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8058HexaneHCID 86615128tert-Butyl 3-(2,2-dibromovinyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 21963855tert-Butyl 3-ethynylpiperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,2-Dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.42 mmol) in THF (1 ml) wad added at −78° C., 0.5 ml of n-BuLi 2.5 M in hexane (1.23 mmol). After 1 h at −78° C., the reaction mixture was quenched with 1 ml of water and the aqueous phase was extracted with AcOEt. The combined organic phase was dried over K2CO3, filtered and evaporated to give 80 mg (93%) of 3-Ethynyl-piperidine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. customthe reaction mixture was quenched with 1 ml of water
  2. extractionthe aqueous phase was extracted with AcOEt
  3. dry with materialThe combined organic phase was dried over K2CO3
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bb934716e89d4c329cbf7dae1075806f
Source dataset
uspto-grants-2010_11
Patent number
US07834035B2

Reaction notes

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