Formaldehyde → (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-methylpyrrolidine

HRID 1280797Notes

Reaction equation

HRID 1280797 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][NH:11][C@@H:10]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]=O>C(O)=O>[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][N:11]([CH3:31])[C@@H:10]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×

Product 1

HCID 54393576(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-methylpyrrolidineYield 95%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.5 g, 1.24 mmol), formic acid (10 ml) and 37% formaldehyde (7.5 ml) was heated for 3 hours at reflux temperature and evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate (25 ml) and 1 N sodium hydroxide (25 ml). The organic phase was isolated, washed once with water, dried over magnesium sulphate and evaporated in vacuo to give (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethyl-1-methylpyrrolidine (0.49 g, yield: 95%) as a golden oil.

Workup

  1. temperaturewas heated for 3 hours
  2. temperatureat reflux temperature
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in a mixture of ethyl acetate (25 ml) and 1 N sodium hydroxide (25 ml)
  5. customThe organic phase was isolated
  6. washwashed once with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-27266a9a1851466eb0e52ac85593a80d
Source dataset
uspto-grants-2002_09
Patent number
US06451836B1

Reaction notes

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