Formaldehyde → HCID 15657719, compound

HRID 1460573Notes

Reaction equation

HRID 1460573 reaction equation
[CH3:1][NH:2][C@@:3]12[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][C@@H:8]1[CH2:7][CH2:6][CH2:5][CH2:4]2.C=O.[C:19]([BH3-])#N.[Na+]>CO>[CH3:1][N:2]([CH3:19])[C:3]12[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][CH:8]1[CH2:7][CH2:6][CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 15657695HCID 15657695, compound

Product 1

HCID 15657719HCID 15657719, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound obtained in Example 4 (1.0 g) in methanol (15 ml) was added aqueous formaldehyde (5 ml, 35%) and in one batch sodium cyanoborohydride (1 g). The reaction was stirred overnight then the solvent removed in vacuo. The residue was taken up in ether and washed with dilute sodium hydroxide, water and finally 2N HCl. The aqueous acid solution was layered with fresh ether and basified with sodium hydroxide solution. The ether layer was washed with water and brine then dried (NaSO4). The ether layer was reduced in volume then to was added slowly anisopropanolic solution of HCl. The white solid obtained was dried in vacuo to give the title compound (0.81 g, 76%), mp 181°-182° C.

Workup

  1. customthe solvent removed in vacuo
  2. washwashed with dilute sodium hydroxide, water and finally 2N HCl
  3. washThe ether layer was washed with water and brine
  4. dry with materialthen dried (NaSO4)
  5. additionto was added slowly anisopropanolic solution of HCl
  6. customThe white solid obtained
  7. customwas dried in vacuo

Sources & evidence

ORD record
ord-194047f5d5724ad3b03f27fab0da4938
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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