D-Psicose → HCID 10104711, compound

HRID 1280799Notes

Reaction equation

HRID 1280799 reaction equation
C([O:8][C@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[CH2:12][N:11]([CH2:22][C:23]([F:26])([F:25])[F:24])[C@@H:10]1[CH2:27][O:28]CC1C=CC=CC=1)C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.[Pd]>[OH:8][C@H:9]1[C@H:13]([OH:14])[CH2:12][N:11]([CH2:22][C:23]([F:26])([F:24])[F:25])[C@@H:10]1[CH2:27][OH:28]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 54509905HCID 54509905, compound2×

Product 1

HCID 10104711HCID 10104711, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethyl-1-(2,2,2-trifluoroethyl)pyrrolidine (Compound 6) (0.3 g, 0.6 mmol) was dissolved in 96% ethanol (30 ml), and 10% Pd/C (0.1 g) was added under N2. The compound was reduced in a Parr apparatus (40 Psi) for 16 hours. The reaction mixture was filtered and evaporated in vacuo giving (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-1-(2,2,2-trifluoroethyl)pyrrolidine (0.09 g) as an brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-b745495e755749d48250012f6b2d24d4
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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