Sodium Sulfate → HCID 52913014, compound

HRID 1944095Notes

Reaction equation

HRID 1944095 reaction equation
C([O:3][C:4]([CH:6]1[C:8]2([C@@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:10]([C:38]3[CH:43]=[CH:42][C:41](Cl)=[C:40]([CH2:45][C:46]4[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH3:54])=[CH:48][CH:47]=4)[CH:39]=3)[O:9]2)[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:31]([O:30][C@@H:11]1[C@@H:12]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2([CH:6]([CH2:4][OH:3])[CH2:7]2)[O:9][C@H:10]1[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([O:52][CH2:53][CH3:54])=[CH:48][CH:47]=2)[CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2×HCID 67074957HCID 67074957, compound

Product 1

HCID 52913014HCID 52913014, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5S,6S,7R,8S)-6,7,8-tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-1-carboxylic acid ethyl ester (350 mg, 0.46 mmole) in dry tetrahydrofuran (5 mL), lithium aluminium hydride (36 mg, 9.3 mmole) was added at 0° C. and stirred for 4 hours. The excess lithium aluminium hydride was decomposed by adding saturated aqueous sodium sulfate and extracted with Ethyl acetate (3×15 mL). The crude product obtained after the removal of solvent furnished 300 mg mixture of {(5S,6S,7R,8S)-6,7,8-Tris-benzyloxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-1-yl}-methanol and {(5S,6S,7R,8S)-6,7,8-Tris-benzyloxy-5-(3-[4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-1-yl}-methanol.

Workup

  1. extractionextracted with Ethyl acetate (3×15 mL)
  2. customThe crude product obtained
  3. customafter the removal of solvent

Sources & evidence

ORD record
ord-94de4516b4d94d3a9b20d0482a0123d1
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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