Water → HCID 558263, compound

HRID 1982644Notes

Reaction equation

HRID 1982644 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[CH2:10][OH:11])=[O:4].[H-].[Na+].O>O1CCCC1>[CH2:10]1[CH:6]2[CH2:7][CH2:8][CH2:9][N:5]2[C:3](=[O:4])[CH2:2][O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 450807952-Pyrrolidinemethanol, 1-(chloroacetyl)-, (2S)-

Product 1

HCID 558263HCID 558263, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(Chloroacetyl)-2-pyrrolidinemethanol, 12 g (0.068 mol), is dissolved in 500 ml of tetrahydrofuran, the solution is cooled to 0°-5° C., and 3.96 g (0.099 mol) of 60% sodium hydride in mineral oil dispersion is slowly added. The mixture is allowed to reach room temperature and is stirred for 14 hours. Water, 20 ml, is added, the solvents evaporated in vacuo, and the residue suspended in 300 ml of chloroform and washed with 100 ml of water and then a saturated aqueous solution of sodium chloride, 2×200 ml. The chloroform layer is separated, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (95:5) to give tetrahydro-1H-pyrrolo[2,1-c][1,4]oxazin-4-(3H)-one, 4.4 g; mp 63.5°-66°.

Workup

  1. temperaturethe solution is cooled to 0°-5° C.
  2. customto reach room temperature
  3. customthe solvents evaporated in vacuo
  4. washwashed with 100 ml of water
  5. customThe chloroform layer is separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue is purified by chromatography
  9. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-06bf76e54d7a47c9bf3946d706e5c115
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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