Tetrahydrofuran → (4-Oxaspiro[2,4]heptane-6-yl)aminopropanol

HRID 1969402Notes

Reaction equation

HRID 1969402 reaction equation
[CH2:1]1[C:3]2([CH2:7][CH:6](CS([O-])(=O)=O)[CH2:5][O:4]2)[CH2:2]1.[NH2:13]CCCO.[CH2:18]1C[O:21][CH2:20][CH2:19]1>>[CH2:2]1[C:3]2([CH2:7][CH:6]([NH:13][CH:20]([OH:21])[CH2:19][CH3:18])[CH2:5][O:4]2)[CH2:1]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 90863-Amino-1-propanolHCID 86640794HCID 86640794, compound

Product 1

HCID 67296698(4-Oxaspiro[2,4]heptane-6-yl)aminopropanolYield 93%

Procedure

To a solution of (4-oxaspiro[2.4]heptane-6-yl)methanesulfonate (336 mg, 1.75 mmol) in dry THF (3 mL) was added 3-aminopropan-1-ol (656.3 mg, 8.75 mmol, TCI). The reaction was refluxed overnight. The mixture was concentrated in vacuo to give a brown residue, which was chromatographed with a silica gel column (8:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (280 mg, 93%).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a brown residue, which
  4. customwas chromatographed with a silica gel column (8:1 (v/v) EtOAc/MeOH)

Sources & evidence

ORD record
ord-c05ccc4b251f4ba2b46efe0badab152d
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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