Trimethylphosphine → HCID 70075766, compound

HRID 1872460Notes

Reaction equation

HRID 1872460 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:25][CH2:26][CH:27]=[CH2:28])[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].P(C)(C)C>C1COCC1.O.CCOCC>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([O:25][CH2:26][CH:27]=[CH2:28])[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

6

Reactant 2

HCID 68983TrimethylphosphineHCID 86755670HCID 86755670, compound

Product 1

HCID 70075766HCID 70075766, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,2R,3R,5R,6S)-3-allyloxy-2-azido-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIII-2) (101 mg, 0.262 mmol) in THF (3.9 mL) and H2O (0.4 mL) was added Me3P (0.29 mL, 0.29 mmol, 1 M sol. in THF) and stirring was continued at 23° C. for 3 h. The reaction mixture was diluted with ether, washed with sat. NaHCO3 -sol., brine and dried over Na2SO4. The crude product was purified by silica gel column chromatography with hexane/EtOAc 1:1 (+small amount of Et3N) to give (1S,2R,3R,5R,6S)-3-allyloxy-2-amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XXIV-2) (47 mg, 50%) as a light brown oil. 1H-NMR (250 MHz, CDCl3) □1.24 (3H, t, J=7.1 Hz), 1.76 (1H, t, J=3.5 Hz), 1.93 (2H, bs), 1.99 (1H, m), 2.07-2.18 (2H, m), 2.31 (1H, dd, J=12.5, 7 Hz), 3.45 (1H, bt, J=8 Hz), 3.93 (2H, bd,J=6 Hz), 4.12 (2H, q, J=7.1 Hz), 5.10-5.35 (4H, m), 5.78 (1H, m), 7.28-7.38 (5H, m); MS[ISP] 360 [(M+H)+ ]; □D20 -10.67° (c=1.00, CHCl3).

Workup

  1. washwashed with sat. NaHCO3 -sol
  2. dry with material, brine and dried over Na2SO4
  3. customThe crude product was purified by silica gel column chromatography with hexane/EtOAc 1:1 (+small amount of Et3N)

Sources & evidence

ORD record
ord-aeed9f732c8c4da09ff3a773b2fa75e0
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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