HCID 59875628, compound → HCID 59875625, compound

HRID 849837Notes

Reaction equation

HRID 849837 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]([CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1)/[CH:9]=[CH:10]/[CH:11]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]>F.C(#N)C>[C:1]([O:5][C:6](=[O:39])[NH:7][C@H:8]([CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1)/[CH:9]=[CH:10]/[CH:11]([CH2:19][OH:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59875628HCID 59875628, compound

Product 1

HCID 59875625HCID 59875625, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14917Hydrofluoric AcidSolvent

Procedure

((1R,2E)-4-(tert-Butyldimethylsilanyloxymethyl)-1-(2-naphthyl)methyl-5-phenylpent-2-enyl)carbamic acid tert-butyl ester (0.75 g, 1.38 mmol) was dissolved in 2% hydrogen fluoride in acetonitrile (50 ml) and stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was chromatographed on silica (80 g) using dichloromethane/heptane/methanol (4/10/1) as eluent. Three fractions were isolated containing compounds with Rf 0.1-0.2. The major fraction (eluting second) was concentrated in vacuo to give 0.35 g of ((1R,2E)-4-hydroxymethyl-1-(2-naphthyl)methyl-5-phenylpent-2-enyl)carbamic acid tert butyl ester as a mixture of diastereomers.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica (80 g)
  3. customThree fractions were isolated
  4. additioncontaining compounds with Rf 0.1-0.2
  5. washThe major fraction (eluting second)
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-ffd5fd7e2e3e48099fd05d0f2afc0a27
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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