Benzoic Acid → (3S,3aR,6aS)-hexahydrofuro[2,3-b]furan-3-yl benzoate

HRID 984530Notes

Reaction equation

HRID 984530 reaction equation
[O:1]1[C@@H:5]2[O:6][CH2:7][CH2:8][C@@H:4]2[C@@H:3]([OH:9])[CH2:2]1.[C:10](O)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:10]([O:9][C@H:3]1[C@@H:4]2[C@@H:5]([O:6][CH2:7][CH2:8]2)[O:1][CH2:2]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11819104(3R,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol

Product 1

HCID 69213652(3S,3aR,6aS)-hexahydrofuro[2,3-b]furan-3-yl benzoateYield 5.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(3R,3aR,6aS)-Hexahydrofuro[2,3-b]furan-3-ol (125 mg) obtained in Example 25 was dissolved in toluene (2 mL). Benzoic acid (214 mg), a 40 wt % solution (705 mg) of diethyl azodicarboxylate in toluene, and triphenylphosphine (416 mg) were added. The mixture was stirred overnight. After the reaction, 10% of the solution was purified by flash chromatography to give the title compound (12 mg) (88% ee), which was almost a pure anti-form.

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-232ed5dd78944c3a8ed764fccb15f10b
Source dataset
uspto-grants-2005_03
Patent number
US06867321B2

Reaction notes

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