Hydrochloric Acid → (2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-[4-isopropyl-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-phenyl]-tetrahydro-pyran-3,4,5-triol

HRID 72631Notes

Reaction equation

HRID 72631 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:19]3[CH:20]=[C:21]([C@H:28]4[C@H:33]([OH:34])[C@@H:32]([OH:35])[C@H:31]([OH:36])[C@@H:30]([CH2:37][OH:38])[O:29]4)[CH:22]=[CH:23][C:24]=3[CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[OH:38][CH2:37][C@@H:30]1[C@@H:31]([OH:36])[C@H:32]([OH:35])[C@@H:33]([OH:34])[C@H:28]([C:21]2[CH:22]=[CH:23][C:24]([CH:25]([CH3:27])[CH3:26])=[C:19]([CH2:18][C:15]3[CH:16]=[C:17]4[C:12]([CH2:11][CH2:10][CH2:9][NH:8]4)=[CH:13][CH:14]=3)[CH:20]=2)[O:29]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913740HCID 52913740, compound

Product 1

HCID 52913632(2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-[4-isopropyl-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-phenyl]-tetrahydro-pyran-3,4,5-triolYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution (2S,3R,4R,5S,6R)-2-[3-(1-benzyl-1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-4-isopropyl-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (1.0 g, 1.0 mmol) in methanol (20 mL) was added 10% dry palladium on charcoal (200 mg) and conc. HCl (0.2 mL), and the mixture was stirred under hydrogen balloon pressure for 18 h. The reaction mixture was filtered through a celite bed which was washed with methanol and the filtrate was concentrated. The resulting residue was purified by preparative HPLC to furnish (2R,3S,4R,5R,6S)-2-Hydroxymethyl-6-[4-isopropyl-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethyl)-phenyl]-tetrahydro-pyran-3,4,5-triol (320 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a celite bed which
  2. washwas washed with methanol
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5c408fc581574264a9ca3b237ec12a6b
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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