HCID 67480625, compound → HCID 15659773, compound

HRID 2273032Notes

Reaction equation

HRID 2273032 reaction equation
[NH2:1][CH:2]1[CH:7]([O:8]CC2C=CC=CC=2)[CH:6]([O:16]CC2C=CC=CC=2)[CH:5]([CH2:24][O:25]CC2C=CC=CC=2)[CH2:4][CH:3]1[OH:33]>CO.C(O)(=O)C.[Pd]>[NH2:1][CH:2]1[CH:3]([OH:33])[CH2:4][CH:5]([CH2:24][OH:25])[CH:6]([OH:16])[CH:7]1[OH:8]

Participants

5

Reactant 1

HCID 67480625HCID 67480625, compound

Product 1

HCID 15659773HCID 15659773, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of Intermediate B (86.5 mg, 0.194 mmol) in MeOH (3 mL) and acetic acid (1 mL) was added Pd/C (10%, 102 mg, 0.097 mmol). The mixture was hydrogenated at 50 psi and at room temperature for 8 h. Catalyst was removed by filtration and solvents were evaporated under reduced pressure to give the product rac-(1R,2R,3S,4S,6R)-3-amino-6-(hydroxymethyl)cyclohexane-1,2,4-triol as the acetic acid salt (46 mg, 100%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 4.07 (brs, 1H), 3.66-3.58 (m, 3H), 3.20 (t, J=9.5 Hz, 1H), 2.85 (brs, 1H), 1.93-1.85 (m, 2H), 1.86 (s, 3H), 1.42 (t, J=13.8 Hz, 1H).

Workup

  1. customCatalyst was removed by filtration and solvents
  2. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-fd4f54648c854dbc84d821a6c274113a
Source dataset
uspto-grants-2015_09
Patent number
US09120781B2

Reaction notes

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