HCID 67870838, compound → HCID 14206137, compound

HRID 329504Notes

Reaction equation

HRID 329504 reaction equation
[CH2:1]([NH:18][C:19](=[O:36])[O:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][O:23][C@H:22]1[CH2:27][O:28]CC1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[H][H]>CO.[Pd]>[CH2:1]([NH:18][C:19](=[O:36])[O:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][O:23][C@H:22]1[CH2:27][OH:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 67870838HCID 67870838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14206137HCID 14206137, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.800 g of dl-trans-2-benzyloxymethyltetrahydropyran-3-yl N-heptadecylcarbamate (prepared as described in Preparation 3) were dissolved in 120 ml of methanol and allowed to react with hydrogen at room temperature for 8 hours in the presence of 10% w/w palladium on activated carbon in a Paal's apparatus at 4 atmospheres (about 4 bar). The catalyst was then filtered off, and the solvent was removed from the filtrate by distillation under reduced pressure, to give 2.729 g of the title compound as a white solid, melting at 84°-86° C. (after recrystallization from diethyl ether).

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solvent was removed from the filtrate by distillation under reduced pressure
  3. customto give
  4. custom2.729 g of the title compound as a white solid, melting at 84°-86° C. (after recrystallization from diethyl ether)

Sources & evidence

ORD record
ord-05559a8242144976ab3806664a8af996
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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