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

HRID 1459636Notes

Reaction equation

HRID 1459636 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 1N 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 1N 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-3ebc3f2e70bc492ba11aa80e18cbb1f3
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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