Formaldehyde → HCID 54555941, compound

HRID 413649Notes

Reaction equation

HRID 413649 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17](N)[CH:16]=2)=[CH:11][CH:10]=1)=[O:8].C=O.[CH3:33][C@H](OC1C=CC(O)=C(N(C)C)C=1)CCCCCC>C(#N)C.C(O)(=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17]([N:2]([CH3:1])[CH3:33])[CH:16]=2)=[CH:11][CH:10]=1)=[O:8]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 53656749HCID 53656749, compoundHCID 53699510HCID 53699510, compound

Product 1

HCID 54555941HCID 54555941, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium cyanoborohydride (202 mg, 3.20 mmol), compound 62 (380 mg, 1.07 mmol), glacial acetic acid (2×0.09 ml), and aqueous formaldehyde (1.28 ml, 16.0 mmol) in 35 ml acetonitrile were reacted according to the procedure for compound 57. Evaporation of solvent yielded 321 mg (78%) of a white solid. The crude product was used without purification.

Workup

  1. customEvaporation of solvent

Sources & evidence

ORD record
ord-e078a60824964eac9420ff3a436f1691
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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