Hydrazine hydrate (1:1) → HCID 86731684, compound

HRID 1504802Notes

Reaction equation

HRID 1504802 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]1.O.NN.O.O.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>CO>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[NH2:3][CH2:12][C:13]1([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 61373Oxalic acid dihydrateHCID 86731685HCID 86731685, compound

Product 1

HCID 86731684HCID 86731684, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]cyclopropyl}carbamate (80.0 g, 253 mmol) in methanol (1600 mL) was added hydrazine hydrate (80% solution in water, 15.9 g, 320 mmol). The reaction mixture was heated to reflux. After 4 hours, the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was washed with DCM (3×500 mL) and then the combined organic layers were concentrated under reduced pressure. This residue was dissolved in diethyl ether (1000 mL) and diluted with oxalic acid dihydrate (solution in ethanol, 35.2 g, 279 mmol), which was added dropwise. After 1 hour, the precipitated solids were collected by filtration, washed with diethyl ether (4×200 mL), and dried to give tert-butyl [1-(aminomethyl)cyclopropyl]carbamate oxalate salt. MS ESI calc'd. for C9H19N2O2 [M+H]+ 187. found 187. 1H NMR (400 MHz, D2O) δ 2.98 (s, 2H), 1.36-1.30 (m, 9H), 0.81 (s, 4H).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed with DCM (3×500 mL)
  4. concentrationthe combined organic layers were concentrated under reduced pressure
  5. dissolutionThis residue was dissolved in diethyl ether (1000 mL)
  6. additionwas added dropwise
  7. waitAfter 1 hour
  8. filtrationthe precipitated solids were collected by filtration
  9. washwashed with diethyl ether (4×200 mL)
  10. customdried

Sources & evidence

ORD record
ord-f49f0a800f7244cc8fbce352d0a25aa1
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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