Methanol → (2R,3S,5S)-5-((1S,3S)-1-Hydroxymethyl-3-hydroxymethyl-4-methylpentyl)-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 500012Notes

Reaction equation

HRID 500012 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C@@H:13](O)[CH2:14][C@H:15]([CH2:19][O:20]CC2C=CC=CC=2)[CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10]([CH:29]([CH3:31])[CH3:30])[C@@H:9]1[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:33]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:46][OH:47]>[Pd]>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C@@H:13]([CH2:46][OH:47])[CH2:14][C@H:15]([CH2:19][OH:20])[CH:16]([CH3:17])[CH3:18])[CH2:11][C@@H:10]([CH:29]([CH3:31])[CH3:30])[C@@H:9]1[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:33]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 67304985(2R,3S,5S)-5-((1S,3S)-3-Benzyloxymethyl-1-hydroxy-4-methyl-pentyl)-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11998866(2R,3S,5S)-5-((1S,3S)-1-Hydroxymethyl-3-hydroxymethyl-4-methylpentyl)-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 0.48 g of 8 in 1.5 mL of methanol is treated with 0.1 g of 10% palladium on charcoal. The suspension is stirred under an atmosphere of hydrogen until the uptake is stable. The suspension is filtered and the solid washed with 5 mL of methanol in two portions. Removal of the solvent in vacuum provides alcohol 9 as an oil. A negative [a]d (e.g. −34.1, −34.6) is found at c=1, CHCl3.

Workup

  1. filtrationThe suspension is filtered
  2. washthe solid washed with 5 mL of methanol in two portions
  3. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-650f257124b44fc8a21498f67ec4b4bc
Source dataset
uspto-grants-2010_08
Patent number
US07767831B2

Reaction notes

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