Benzaldehyde → HCID 10036538, compound

HRID 1459646Notes

Reaction equation

HRID 1459646 reaction equation
Cl.[OH:2][C@@H:3]1[C@@H:7](CO)[C@@H:6]([CH2:10][OH:11])CN1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]([BH3-])#[N:21].[Na+].Cl.C[OH:26]>C(OCC)C>[CH2:12]([N:21]1[CH2:20][C@@H:3]([OH:2])[C@H:7]([OH:26])[C@H:6]1[CH2:10][OH:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 69966456HCID 69966456, compound2×

Product 1

HCID 10036538HCID 10036538, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2R,3R,4R)-2-Hydroxy-3,4-dihydroxymethylpyrrolidine hydro-chloride (compound 2) (0.265 g, 1.6 mmol) was dissolved in dry methanol (25 ml), and benzaldehyde (0.159 ml, 1.6 mmol) and sodium cyanoborohydride (0.098 g, 1.6 mmol) was added. A solution of anhydrous hydrogen chloride in diethylether (2M) was added dropwise until pH 6. The resulting mixture was stirred for 24 hours at room temperature under a nitrogen atmosphere and evaporated in vacuo. Purification of the product on silica gel (Eluent: 2-propanol/methanol (4:1)) afforded (2R,3R,4R)-1-benzyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine (0.304 g, yield: 87%) as an oil.

Workup

  1. customevaporated in vacuo
  2. customPurification of the product on silica gel (Eluent: 2-propanol/methanol (4:1))

Sources & evidence

ORD record
ord-e500794db9334c57bd5195d4b4303d15
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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