Formaldehyde → (2S)-2-(4-Methoxybenzylthiomethyl)-1-methylpyrrolidine

HRID 1030169Notes

Reaction equation

HRID 1030169 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)=[CH:5][CH:4]=1.C=O.[C:19]([BH3-])#N.[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:19])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57043207(2S)-2-(4-methoxybenzylthiomethyl)pyrrolidine

Product 1

HCID 57048351(2S)-2-(4-Methoxybenzylthiomethyl)-1-methylpyrrolidineYield 41.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The procedure described in preparation 5-(4) was repeated, but using 2 g of (2S)-2-(4-methoxybenzylthio-methyl)pyrrolidine, 35% formalin and 848 mg of sodium cyanoborohydride in the presence of 44 ml of acetonitrile, to afford 883 mg of the title compound as an oil.

Workup

  1. customThe procedure described in preparation 5-(4)

Sources & evidence

ORD record
ord-b465e60593454a68a595676a62a833b6
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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