Hydrazine hydrate (1:1) → HCID 22884189, compound

HRID 1598381Notes

Reaction equation

HRID 1598381 reaction equation
[CH2:1]([O:3][C:4]([N:6]([CH2:15][C@H:16]1[O:21][C@@H:20]([CH2:22][N:23]2C(=O)C3=CC=CC=C3C2=O)[CH2:19][CH2:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:5])[CH3:2].O.NN>CO>[NH2:23][CH2:22][C@H:20]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH2:15][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[O:21]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22884192HCID 22884192, compound

Product 1

HCID 22884189HCID 22884189, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the crude cis-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]-2-phthalimidomethyltetrahydropyrane (2.81 g, 6.19 mmol) in methanol (30 ml) was added hydrazine monohydrate (0.48 ml, 15 mmol) and heated under reflux for 2 hours. To the reaction mixture was added purified water (30 ml) to dissolve insolubles and the ethanol was distilled off under reduced pressure. The aqueous layer was extracted with chloroform (50 ml×3). The combined organic layer was dried over potassium carbonate and the solvent was distilled off under reduced pressure to give crude cis-2-aminomethyl-6-[N-ethoxycarbonyl-N-(p-fluorobenzyl)aminomethyl]tetrahydropyrane (2.0 g). This compound was used for the subsequent reaction without purification. Yield of two steps=100%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. additionTo the reaction mixture was added
  4. custompurified water (30 ml)
  5. dissolutionto dissolve insolubles
  6. distillationthe ethanol was distilled off under reduced pressure
  7. extractionThe aqueous layer was extracted with chloroform (50 ml×3)
  8. dry with materialThe combined organic layer was dried over potassium carbonate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-302e50e6b7ce4d05b585b376ee845fb1
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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