Formaldehyde → HCID 69334832, compound

HRID 1003191Notes

Reaction equation

HRID 1003191 reaction equation
[CH2:1]([O:8][C:9]1[C:26](N)=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:28])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]=O.[C:31]([BH3-])#[N:32].[Na+].[NH4+].[Cl-]>C1COCC1.CC#N>[CH2:1]([O:8][C:9]1[C:26]([N:32]([CH3:31])[CH3:29])=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:28])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydride2×HCID 69334834HCID 69334834, compound

Product 1

HCID 69334832HCID 69334832, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-benzyloxy-2-aminoestra-1,3,5(10)-trien-17-one (80, 0.751 g, 2.0 mmol) in THF (2.0 mL) and CH3CN (10 mL) were added 37% aqueous formaldehyde (4.0 mL) and sodium cyanoborohydride (0.377 g, 6.0 mmol) and stirred for 2 h at room temperature. Additional sodium cyanoborohydride (0.377 g, 6.0 mmol) was then added to the reaction mixture, which mixture was then stirred for 20 h. Next, saturated aqueous NH4Cl at 0° C., was added to the reaction mixture, and it was then extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:THF (5:1→3:1, v/v) to afford 0.797 g of 81 (99% yield) mp: 165-166° C.

Workup

  1. stirringwas then stirred for 20 h
  2. extractionwas then extracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-29e2fd2fcaae41b396c219987268aa3a
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

Loading…