Triphenylphosphine → HCID 86753021, compound

HRID 482098Notes

Reaction equation

HRID 482098 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:34]=[C:35]([O:43][S:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[Cl:53])(=[O:46])=[O:45])[CH:36]=[C:37]([C:39]([O:41][CH3:42])=[O:40])[CH:38]=1.[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][CH:64]([CH2:67]O)[CH2:63][CH2:62]1)=[O:60])([CH3:57])([CH3:56])[CH3:55]>O1CCCC1>[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][CH:64]([CH2:67][O:32][C:33]2[CH:34]=[C:35]([O:43][S:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[Cl:53])(=[O:46])=[O:45])[CH:36]=[C:37]([C:39]([O:41][CH3:42])=[O:40])[CH:38]=2)[CH2:63][CH2:62]1)=[O:60])([CH3:57])([CH3:55])[CH3:56]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 53882575HCID 53882575, compound

Product 1

HCID 86753021HCID 86753021, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphine (0.249 g, 0.95 mol) in tetrahydrofuran (20 mL) was treated with diethyl azodicarboxylate (0.131 mL, 0.83 mol) and allowed to stir at ambient temperature for 15 min. before the addition of 2-chlorobenzenesulfonic acid 3-hydroxy-5-carbomethoxyphenyl ester (0.25 g, 0.73 mol), as prepared in the preceding step, in tetrahydrofuran (5 mL) and N-tert-butoxycarbonyl-4-piperidinemethanol (0.165 g, 0.77 mol), as prepared in step f of Example 1. The reaction mixture was allowed to stir at ambient temperature overnight. The solvent was evaporated and treated with ether/hexane to produce a crystalline material, which was separated by filtration. The filtrate was evaporated to an oil, placed on a silica gel column, and eluted with 20% ethyl acetate/hexane. The appropriate fractions were evaporated to give 0.14 g of material. 1H-NMR (CDCl3 ; 300 MHz): δ 1.25 (m, 3H), 1.47 (s, 9H), 1.78 (m, 2H), 2.74 (t, 2H), 3.77 (d, 2H), 3.88 (s, 3H), 4.12 (m, 2H), 6.90 (t, 1H), 7.38 (m, 3H), 7.62 (m, 2H), 7.97 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. additiontreated with ether/hexane
  3. customto produce a crystalline material, which
  4. customwas separated by filtration
  5. customThe filtrate was evaporated to an oil
  6. washeluted with 20% ethyl acetate/hexane
  7. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-9d7041d2958b4fd8b39d50096f755c4a
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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