Triphenylphosphine → HCID 69157502, compound

HRID 1624278Notes

Reaction equation

HRID 1624278 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86590310HCID 86590310, compound

Product 1

HCID 69157502HCID 69157502, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-1-azido-4-(tert-butoxycarbonylamino)-2-cyclohexene (1.14 g, 4.79 mmol) in THF (50 mL) and water (5 mL) was added triphenylphosphine (2.60 g, 10 mmol) and the mixture was stirred at room temperature for 20 hours. The mixture was concentrated and the thus obtained material was purified by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH) followed by radial chromatography on silica gel (2 mm plate, 100:1:1 CH2Cl2—CH3OH—NH4OH) and provided 0.32 g (31%) of trans-1-amino-4-(tert-butoxycarbonylamino)-2-cyclohexene as a colorless oil. 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.50-1.92 (m, 2H), 1.99-2.10 (m, 2H), 3.32 (br s, 1H), 4.10-4.19 (m, 1H), 4.47-4.60 (m, 1H), 5.57-5.77 (m, 2H);

Workup

  1. concentrationThe mixture was concentrated
  2. customthe thus obtained material was purified by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-d79e2fa2fd5a4c78ae737be1638d1605
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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