Formaldehyde → HCID 178479974, compound

HRID 2099886Notes

Reaction equation

HRID 2099886 reaction equation
[C:1]([SiH2:5][O:6][C:7]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:8]12[CH:23]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[CH:12]([CH:13]([N:15]3[CH:20]=[CH:19][C:18](=[O:21])[NH:17][C:16]3=[O:22])[O:14]1)[O:11][NH:10][CH2:9]2)([CH3:4])([CH3:3])[CH3:2].C=O.[BH3-][C:51]#N.[Na+].CCOC(C)=O>CC(O)=O>[C:1]([SiH2:5][O:6][C:7]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:8]12[CH:23]([O:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[CH:12]([CH:13]([N:15]3[CH:20]=[CH:19][C:18](=[O:21])[NH:17][C:16]3=[O:22])[O:14]1)[O:11][N:10]([CH3:51])[CH2:9]2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 5003444Sodium cyanoborohydrideHCID 178455408HCID 178455408, compound

Product 1

HCID 178479974HCID 178479974, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of compound 52 (1 mmol) in CH3COOH (5 mL) and trithylortoformate (1 mL), 20% aq. HCHO (0.16 mL, 1.1 mmol) was added at 0° C. After 15 minutes NaBH3CN (2 mmol) is added. After an additional 1 hour the mixture is poured into EtOAc (250 mL), washed with saturated aqueous NaHCO3 (2×250 mL), dried over anhydrous Na2SO4, filtered and evaporated. Purification by silica gel chromatography gave compound 53 in 90% isolated yield.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×250 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-b961426fd3c341a880ec9da0c97aec87
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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