Triphenylphosphine → HCID 86755674, compound

HRID 1872467Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH:8]=[CH:9][C@:10]2([N:22]=[N+]=[N-])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH:8]=[CH:9][C@:10]2([NH2:22])[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (1S,2R,5R,6S)-2-azido-bicyclo [3.1.0]hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXVI) (66 mg, 0.202 mmol) in THF (4.5 mL) and H2O (0.5 mL) was added polymer supported PPh3 (130 mg, 0.404 mmol, 3.1 mmollg) and the mixture was stirred at 60° C. for 19 h. The resin was filtered off and washed with DCM. Removal of the solvent in vacuum left a yellow oil which was purified by silica gel column chromatography with hexane/ethyl acetate 1:3 to give (1S,2R,5R,6S) -2-amino-bicyclo [3.1.0] hex-3-ene-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXVII) (19 mg, 31%) as a colorless oil. 1H-NMR (250 MHz, CDCl3) □1.25 (3H, t, J=7.2 Hz), 1.55 (1H, t, J=2.9 Hz), 1.78 (2H, bs), 2.53 (2H, m),4.12 (2H, q,J=7.2 Hz), 5.21 (2H, s), 5.37 (1H, d,J=5.3 Hz), 6.07 (1H, dd,J=5.3, 2 Hz), 7.35 (5H, s); MS[ISP] 302 (M+H+); □D20 -322.98 (c=0.77, CHCl3).

Workup

filtrationThe resin was filtered off
washwashed with DCM
customRemoval of the solvent in vacuum
waitleft a yellow oil which
customwas purified by silica gel column chromatography with hexane/ethyl acetate 1:3

Sources & evidence

ORD record: ord-c47d790397764bedb4afba33a39f3c19
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107342

Reaction notes

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