Triphenylphosphine → Di-tert-butyl 1-(cyclopropylmethyl)hydrazine-1,2-dicarboxylate

HRID 1931073Notes

Reaction equation

HRID 1931073 reaction equation
[CH:1]1([CH2:4]O)[CH2:3][CH2:2]1.[NH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O>C1COCC1>[CH:1]1([CH2:4][N:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 85431Di-tert-butyl bicarbamateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate

Product 1

HCID 66643119Di-tert-butyl 1-(cyclopropylmethyl)hydrazine-1,2-dicarboxylateYield 354.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of cyclopropylmethanol (7.15 mL, 90 mmol), di-tert-butyl hydrazine-1,2-dicarboxylate (6.30 g, 27.1 mmol) and triphenylphosphine (28.5 g, 109 mmol) in THF (100 mL) was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (25 g, 109 mmol) in portions at ambient temperature. The reaction mixture was concentrated and allowed to stand overnight. The white solid (PPh3O) precipitated was filtered off and the filtrate was purified by flash chromatography (silica gel, EtOAc in Hexane in 5-25% gradient) to yield 27.5 g (96%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe white solid (PPh3O) precipitated
  3. filtrationwas filtered off
  4. customthe filtrate was purified by flash chromatography (silica gel, EtOAc in Hexane in 5-25% gradient)

Sources & evidence

ORD record
ord-ebe47acafd0c4c69967434f894b97ce5
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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