Triphenylphosphine → HCID 178445742, compound

HRID 1036415

Reaction equation

HRID 1036415 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:47]([C@H:51]1[CH2:56][CH2:55][C@H:54](O)[CH2:53][CH2:52]1)[CH2:48][CH2:49][CH3:50].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(OCC)(=O)C>[C:23]([O:22][C:21](=[O:27])[NH:20][C:12]1([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][C@H:54]4[CH2:55][CH2:56][C@@H:51]([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:52][CH2:53]4)[CH:3]=3)[CH:8]=2)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44228963Tert-butyl 5-(6-hydroxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 178445814HCID 178445814, compound

Product 1

HCID 178445742HCID 178445742, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5-(6-Hydroxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxinan-5-yl]-carbamic acid tert-butyl ester (Example 13, 498 mg, 0.00133 mol, Apex), PS-triphenylphosphine (3.00 mmol/g loading, 689 mg, 0.00207 mol, Aldrich) were slurried in Tetrahydrofuran (10 mL, Acros), then trans-4-butylcyclohexanol (0.255 g, 0.00163 mol, Synthon) and diisopropyl azodicarboxylate (0.315 mL, 0.00160 mol, Acros) was added. The reaction was stirred at room temperature. After 4 d, the mixture was diluted with ethyl acetate, filtered and concentrated and the crude product was taken up into methylene chloride and subjected to silica gel chromatography purification to give the title compound in 353 mg yield (52%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customsubjected to silica gel chromatography purification

Sources & evidence

ORD record
ord-60b5840853cc4b0695cc28f71ac36825
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Linked notes

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