Triphenylphosphine → HCID 67281300, compound

HRID 2367168Notes

Reaction equation

HRID 2367168 reaction equation
[OH:1][C@H:2]1[C@@H:9]2[C@@H:5]([CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]2)[CH2:4][CH2:3]1.[Cl:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21](O)=[CH:20][CH:19]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.C1CCCCC1>[Cl:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([O:1][C@@H:2]2[C@@H:9]3[C@@H:5]([CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]3)[CH2:4][CH2:3]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 117874-Chloro-1-naphtholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 50986395HCID 50986395, compound

Product 1

HCID 67281300HCID 67281300, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The process is performed according to the procedure described in Example 11, step 11.1. Starting with 0.15 g (0.66 mmol) of tert-butyl (3aR,4R,6aS)-4-hydroxyhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate, obtained in step 13.1., 0.130 g (0.73 mmol) of 4-chloro-1-naphthol, 0.160 g (0.79 mmol) of diisopropyl azodicarboxylate and 0.206 g (0.659 mmol) of resin-supported triphenylphosphine (triphenylphosphine, polymer-supported, 3.2 mmol/g on polystyrene), and after chromatography on silica gel, eluting with a 95/5 and then a 90/10 mixture of cyclohexane and ethyl acetate, 0.077 g (30%) of expected product is obtained.

Workup

  1. customobtained in step 13.1

Sources & evidence

ORD record
ord-7072529a83364b82b72a45204a1ecdf1
Source dataset
uspto-grants-2014_04
Patent number
US08697883B2

Reaction notes

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