Benzoic Acid → (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

HRID 1050247Notes

Reaction equation

HRID 1050247 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:29]1([CH:35]2[O:40][C@H:39]3[CH2:41][C@@H:42](O)[CH2:43][O:44][C@@H:38]3[CH2:37][O:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:20]([O:28][C@@H:42]1[CH2:43][O:44][C@H:38]2[C@@H:39]([O:40][CH:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:36][CH2:37]2)[CH2:41]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 217656031,5-Anhydro-4,6-O-benzylidene-3-deoxy-D-glucitol

Product 1

HCID 90044852(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of triphenylphosphine (560 mg, 2.134 mmol) and benzoic acid (261 mg, 2.134 mmol) under nitrogen in anhydrous THF (8.0 mL) was added (4aR,7R,8aS)-2-phenylhexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (500 mg, 2.134 mmol), then DIAD (0.41 mL, 428 mg, 2.116 mmol) dropwise over 10 minutes. After stirring at room temperature for 1 hour, the mixture was concentrated under reduced pressure. The resultant oil was dissolved in DCM, then loaded directly onto a Biotage™ 50 g (2×25 g in series) silica gel cartridge and eluted with 0-100% EtOAc in 1:1 Hexane/DCM over 25 column volumes. The product fractions were combined and concentrated under reduced pressure to provide the desired product as a white solid. LC-MS: calculated for C20H20O5 340.13, observed m/e: 341.13 (M+H)+ (Rt 2.21/4 min).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe resultant oil was dissolved in DCM
  3. washeluted with 0-100% EtOAc in 1:1 Hexane/DCM over 25 column volumes
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e4417874c144436bf3c814d00ac1960
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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