Ethyl formate → 1-Boc-4-[(1-methyl-4-piperidyl)methyl]piperidine

HRID 1869631Notes

Reaction equation

HRID 1869631 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:27](OCC)=O>O1CCCC1>[CH3:27][N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 21226445Aluminium lithium hydrideHCID 497611974-Piperidin-4-ylmethyl-piperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 688889221-Boc-4-[(1-methyl-4-piperidyl)methyl]piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dimethylethyl 4-(4-piperidinylmethyl)-1-piperidinecarboxylate (may be prepared as described in Description 2) (1.5 g), and LiAlH4 (26.6 ml of 1M solution in tetrahydrofuran) were combined in tetrahydrofuran (10 ml) and the reaction mixture stirred at room temperature for 10 min before cooling to 0° C. in an ice/water bath. Ethyl formate (5 ml) was then added dropwise. The reaction was then quenched with 3 N sodium hydroxide solution. The solid precipitate formed was filtered and washed with more tetrahydrofuran. The combined organics were dried over Na2SO4, and evaporated to give the title compound (D18) (1.1 g).

Workup

  1. temperaturebefore cooling to 0° C. in an ice/water bath
  2. customThe reaction was then quenched with 3 N sodium hydroxide solution
  3. customThe solid precipitate formed
  4. filtrationwas filtered
  5. washwashed with more tetrahydrofuran
  6. dry with materialThe combined organics were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-7cdeab6b0ba04e769d77c58f584344a8
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

Loading…