Formaldehyde → HCID 178479888, compound

HRID 1576746Notes

Reaction equation

HRID 1576746 reaction equation
[CH:1]1[C:6]([C:7]([NH:9][C@H:10]([C:16]([OH:18])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8])=[CH:5][CH:4]=[C:3]([NH:19][CH2:20][CH2:21][C:22]2[N:27]=[C:26]3[C:28]([N:30]=[C:31]([NH2:33])[NH:32][C:25]3=[N:24][CH:23]=2)=[O:29])[CH:2]=1.[CH2:34]1NC2NC(N)=NC(=O)C=2NC1CCNC1C=CC(C(N[C@H](C(O)=O)CCC(O)=O)=O)=CC=1.[H][H].C=O.[BH4-].[Na+]>>[CH3:34][N:27]1[C:26]2[C:28]([N:30]=[C:31]([NH2:33])[NH:32][C:25]=2[NH:24][CH2:23][CH:22]1[CH2:21][CH2:20][NH:19][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@H:10]([C:16]([OH:18])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8])=[CH:1][CH:2]=1)=[O:29]

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compoundHCID 178508908HCID 178508908, compound2×HCID 178508921HCID 178508921, compound2×

Product 1

HCID 178479888HCID 178479888, compound

Procedure

In the preparation of N5 -methyltetrahydrohomofolic acid from homofolic acid, the steps consisting of reducing homofolic acid to tetrahydrohomofolic acid in the dark with a slight overpressure of hydrogen in the presence of reduced platinum oxide, immediately reacting tetrahydrohomofolic acid with formaldehyde to product the intermediate 5,11-methylenetetrahydrohomofolic acid and reducing without isolation the formed 5,11-methylene intermediate with sodium borohydride to give the desired 5-methyltetrahydrohomofolic acid (5-MeTHHF) and removing by precipitation at a pH of about 3.8 with acetic acid the side products, refrigerating the product filtrate containing 5-MeTHHF overnight and separating and recovering 5-MeTHHF.

Sources & evidence

ORD record
ord-33181c30da12410c903ddaf0aeb704d7
Source dataset
uspto-grants-1976_09
Patent number
US03983118

Reaction notes

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