Formaldehyde → HCID 67212526, compound

HRID 1026437Notes

Reaction equation

HRID 1026437 reaction equation
[C:1]1([S:7]([N:10]2[CH2:17][CH:16]3[NH:18][CH:12]([CH2:13][O:14][CH2:15]3)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH3-][C:22]#N.[Na+]>CC#N.CC(O)=O>[CH3:22][N:18]1[CH:12]2[CH2:13][O:14][CH2:15][CH:16]1[CH2:17][N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH2:11]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67212430HCID 67212430, compound

Product 1

HCID 67212526HCID 67212526, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 112f (2.0 g, 7.5 mmol) in MeCN (60 ml) was added HCHO (1.4 ml, 16 mmol) and 5 drops of AcOH at room temperature. Then NaCNBH3 (1 g, 16 mmol) added and the mixture was stirred for 2 h. It was poured onto water and extracted with EA (100*3). The organic layer was dried over Na2SO4, filtered off, evaporated, and purified through a silica gel column eluting with PE:EA=5:1 to 1:1 to give 112g as a colorless oil (1.5 g, 72%) MS: [M+H]+: 283

Workup

  1. additionIt was poured onto water
  2. extractionextracted with EA (100*3)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered off
  5. customevaporated
  6. custompurified through a silica gel column
  7. washeluting with PE

Sources & evidence

ORD record
ord-ec5046462c2b433eaf6a5576c3536ec1
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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