Pyridine → HCID 11954491, compound

HRID 1092444Notes

Reaction equation

HRID 1092444 reaction equation
O[C@:2]1([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:7][C:6](=[O:8])[C@H:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:3]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C=CC=CC=1>C(Cl)Cl>[CH2:26]([O:25][C@H:3]1[C@H:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:5]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:6](=[O:8])[CH:7]=[C:2]1[CH2:33][O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 11028055(2R,3S,4S,5S)-2,3,4-Tris(benzyloxy)-5-[(benzyloxy)methyl]-5-hydroxycyclohexan-1-one

Product 1

HCID 11954491HCID 11954491, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4S,5S,2R)-5-hydroxy-5-[(phenylmethoxy)methyl]-2,3,4-tris(phenyl methoxy)cyclohexan-1-one (580.0 g, 1.051 mol) in anhydrous methylene chloride (3.6 L) was added trifluoroacetic anhydride (331.1 g, 222 mL, 1.577 mol) followed by addition of pyridine (149.7 g, 153 mL, 1.892 mol) at room temperature under argon. The mixture was stirred at room temperature for 24 h and quenched by addition of ice water (1.0 L). The organic layer was separated and the aqueous layer was extracted with methylene chloride (3×2 L). The combined organic layers were washed with sodium bicarbonate (sat. aq. 3×0.5 L), brine (sat. aq. 3×1.0 L), dried over sodium sulfate, filtered and concentrated to give a yellow oil (476.7 g, purity of 90%, yield 85%). 1H NMR (CDCl3, 400 MHz): δ 7.26-7.48 (m, 20H), 6.26 (s, 1H), 5.15 (d, J=11.2 Hz, 1H), 5.05 (d, J=10.8 Hz, 1H), 4.95 (d, J=10.8 Hz, 1H), 4.77-4.81 (m, 2H), 4.72 (d, J=11.2 Hz), 4.55 (S, 2H), 4.40-4.42 (m, 1H), 4.31 (d, J=16 Hz, 1H), 4.03-4.13 (m, 3H).

Workup

  1. customquenched by addition of ice water (1.0 L)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride (3×2 L)
  4. washThe combined organic layers were washed with sodium bicarbonate (sat. aq. 3×0.5 L), brine (sat. aq. 3×1.0 L)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil (476.7 g, purity of 90%, yield 85%)

Sources & evidence

ORD record
ord-92b996d5b6a34162b2f481d135100168
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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