1-Bromo-3-methoxypropane → HCID 66788050, compound

HRID 2381167Notes

Reaction equation

HRID 2381167 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:11][C:12]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[O:13])[CH3:10].Br[CH2:28][CH2:29][CH2:30][O:31][CH3:32]>C1COCC1>[CH2:9]([O:11][C:12]([C:14]1([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 5245511-Bromo-3-methoxypropaneHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 66788050HCID 66788050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a pre-cooled THF solution (200 ml) under an argon atmosphere was added at −5° C. LDA (2M in THF/heptane/ethylbenzene, 16.24 ml) then dropwise piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (4.4 g, 4.2 ml) in THF (50 ml). The mixture was stirred between −5° C. to 0° C. for 3 hour and 1-bromo-3-methoxypropane (4.97 g) was added slowly at 0° C. The mixture was then stirred overnight at RT, the solvent was evaporated off, the residue taken up in ethyl acetate and washed with water then brine. The layers were separated, the organic layer dried over sodium sulphate and then evaporated off to give the desired 4-(3-methoxy-propyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester a light brown oil (6.058 g) oil that was used in next reaction step without further purification.

Workup

  1. stirringThe mixture was then stirred overnight at RT
  2. customthe solvent was evaporated off
  3. washwashed with water
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over sodium sulphate
  6. customevaporated off

Sources & evidence

ORD record
ord-149180be133d4c7bbe90ae164938b1a4
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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