Sodium Hydroxide → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

HRID 1957574Notes

Reaction equation

HRID 1957574 reaction equation
[C:1]([OH:4])(=[O:3])C.[NH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][OH:14])[CH2:7][CH2:6]1.[OH-].[Na+].C(OC(OC[CH2:29][CH2:30][CH3:31])=O)(OCCCC)=O.O1CCOC[CH2:33]1>>[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][OH:14])[CH2:7][CH2:6]1)([O:4][C:30]([CH3:29])([CH3:31])[CH3:33])=[O:3]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 14200314Dibutyl dicarbonateHCID 19068166HCID 19068166, compound

Product 1

HCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Procedure

A stirred solution of 3-2 (41.8 g, 0.14 mol), dioxane (300 mL), and 3N NaOH (0.51 mol, 170 mL) at ambient temperature was treated with di-butyl dicarbonate (32.1 g, 0.15 mol). After 24 h the dioxane was evaporated and the aqueous phase extracted with ether. The ethereal extracts were combined, washed with 10% KHSO4 and brine, dried (MgSO4), and then concentrated. Flash chromatography (silica, 30% to 50% EtOAc/ hexanes) gave 3-3 as an oil, Rf 0.11 (silica, 20% EtOAc/hexanes).

Workup

  1. customAfter 24 h the dioxane was evaporated
  2. extractionthe aqueous phase extracted with ether
  3. washwashed with 10% KHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9dd6916810544efcbddfe8d5c6fe69f3
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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