Phosphate → HCID 57233113, compound

HRID 1492463Notes

Reaction equation

HRID 1492463 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Si:11]([O:28][CH2:29][C@@H:30]1[C@@H:34]([CH2:35][O:36][Si:37]([C:50]([CH3:53])([CH3:52])[CH3:51])([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:33][CH2:32][C:31]1=[O:54])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.P([O-])([O-])([O-])=O.C(Cl)Cl>C1(C)C=CC=CC=1.CCCCCC>[Si:11]([O:28][CH2:29][C@@H:30]1[C@@H:34]([CH2:35][O:36][Si:37]([C:50]([CH3:53])([CH3:52])[CH3:51])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:33][CH2:32][C@@H:31]1[OH:54])([C:24]([CH3:25])([CH3:26])[CH3:27])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 1061PhosphateHCID 6344DichloromethaneHCID 21225700DiisobutylaluminumhydrideHCID 57286114HCID 57286114, compound

Product 1

HCID 57233113HCID 57233113, compoundYield 79,902.203%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

In an atmosphere of argon gas, 1M solution of diisobutylaluminum hydride in toluene (2.7 ml, 2.7 mmoles) was slowly added at -78° C. to solution of (2S,3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentanone (1.40 g, 2.25 mmoles) in toluene (23 ml), and the resulting mixture was stirred at that temperature for 15 minutes. Then, 0.2M phosphate buffer solution (pH 7) was added to the reaction mixture and stirred for a while, after which an excessive amount of methylene chloride was added and the inorganic matter was filtered off. The filtrate was subjected to extraction with methylene chloride and an extract solution was dried on anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:10, v/v) to obtain (1S,2S,3S)-2,3-bis(t-butyldiphenylsilyloxymethyl)-1-cyclopentanol (1,120 g, Yield 80%):

Workup

  1. stirringstirred for a while
  2. filtrationthe inorganic matter was filtered off
  3. extractionThe filtrate was subjected to extraction with methylene chloride
  4. dry with materialan extract solution was dried on anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-383e9229e03b4a19b79012b2ecdf92f9
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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