Tetrahydrofuran → HCID 19888404, compound

HRID 1577015Notes

Reaction equation

HRID 1577015 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([C:9](O)=[O:10])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH-].[Na+]>O>[C:1]([N:5]1[CH2:8][CH:7]([CH2:9][OH:10])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2967221-Tert-butylazetidine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 19888404HCID 19888404, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-t-Butylazetidine-3-carboxylic acid (5.0 g., 0.318 mol.) was added portionwise to a slurry of 1.81 g. (0.0477 mol.) of lithium aluminum hydride in 135 ml. of tetrahydrofuran. The mixture was refluxed for 12 hours, cooled and 2 ml. of water and 2 ml. of 15% aqueous sodium hydroxide were added followed by an additional 6 ml. of water. The mixture was filtered and the precipitate was washed with ether. The filtrate and washings were combined and evaporated to dryness to give N-t-butyl-3-hydroxymethylazetidine, b.p. 124°-127° (27 mm.).

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. washthe precipitate was washed with ether
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e2a355e491804ef993c9496b7afc5e6f
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

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