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

HRID 536708Notes

Reaction equation

HRID 536708 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-2316340816cb4158a2fdf9fa21d25c48
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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