Hydrazine hydrate (1:1) → tert-butyl ((3R,4S)-4-aminotetrahydrofuran-3-yl)carbamate

HRID 56396Notes

Reaction equation

HRID 56396 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[C@@H:12]1[CH2:16][O:15][CH2:14][C@@H:13]1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].O.NN>C(O)C>[NH2:3][C@@H:12]1[CH2:16][O:15][CH2:14][C@@H:13]1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 118043449Tert-butyl ((3R,4S)-4-(1,3-dioxoisoindolin-2-yl)tetrahydrofuran-3-yl)carbamate

Product 1

HCID 90436776tert-butyl ((3R,4S)-4-aminotetrahydrofuran-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Tert-butyl ((3R,4S)-4-(1,3-dioxoisoindolin-2-yl)tetrahydrofuran-3-yl)carbamate (13.08 g, 39.4 mmol) was dissolved into ethanol (98 mL, 0.4 M)). Hydrazine monohydrate (1.97 g, 39.4 mmol) was added, and the reaction was stirred 30 minutes at 50° C. and then 2 hours at 75° C. The reaction was then cooled to room temperature and the white solid was removed by filtration. The filtrate was concentrated down and dried, then treated with ethanol (about 15 mL). Additional white solid was removed by filtration, then filtrate was concentrated down and dried to yield tert-butyl ((3R,4S)-4-aminotetrahydrofuran-3-yl)carbamate as a thick, clear oil (8.724 g at 90% purity; 99%).

Workup

  1. custom2 hours
  2. customat 75° C
  3. temperatureThe reaction was then cooled to room temperature
  4. customthe white solid was removed by filtration
  5. concentrationThe filtrate was concentrated down
  6. customdried
  7. additiontreated with ethanol (about 15 mL)
  8. customAdditional white solid was removed by filtration
  9. concentrationfiltrate was concentrated down
  10. customdried

Sources & evidence

ORD record
ord-069b00405ec548c5827087cf01c35a5e
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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