Sodium triacetoxyborohydride → HCID 68449802, compound

HRID 2233188Notes

Reaction equation

HRID 2233188 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[C:19]3[C:20]4[N:11]([C:12](=[O:22])[CH:13]=[N:14][C:15]=4[CH:16]=[CH:17][C:18]=3[F:21])[CH2:10]2)[CH2:4][CH2:3]1.[CH:23]([C:25]1[N:41]=[CH:40][C:28]2[O:29][CH2:30][CH2:31][N:32]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:27]=2[CH:26]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO>[F:21][C:18]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][C:12](=[O:22])[N:11]3[CH2:10][CH:9]([CH2:8][N:5]4[CH2:4][CH2:3][CH:2]([NH:1][CH2:23][C:25]5[N:41]=[CH:40][C:28]6[O:29][CH2:30][CH2:31][N:32]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[C:27]=6[CH:26]=5)[CH2:7][CH2:6]4)[C:19]=1[C:20]=23

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 68445055HCID 68445055, compoundHCID 86623073HCID 86623073, compound

Product 1

HCID 68449802HCID 68449802, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of 6-[(4-amino-1-piperidinyl)methyl]-7-fluoro-5,6-dihydro-3H-pyrrolo[1,2,3-de]quinoxalin-3-one (95 mg, 0.31 mmol) and 1,1-dimethylethyl 7-formyl-2,3-dihydro-1H-pyrido[3,4-b][1,4]oxazine-1-carboxylate (83 mg, 0.31 mmol) in chloroform/methanol (1:1, 8 ml) was stirred with molecular sieves overnight, then heated under reflux for 3 h. After cooling, sodium triacetoxyborohydride (164 mg) was added and the mixture was stirred for 5 h at room temperature. The mixture was basified and the aqueous phase was extracted with 10% methanol/dichloromethane. Combined organic fractions were dried and evaporated. Chromatography on silica, eluting with 0-20% (2M ammonia in methanol)/dichloromethane, gave impure material. Further chromatography on silica, eluting with 0-10% methanol/dichloromethane, gave the pure product (91 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase was extracted with 10% methanol/dichloromethane
  5. customCombined organic fractions were dried
  6. customevaporated
  7. washChromatography on silica, eluting with 0-20% (2M ammonia in methanol)/dichloromethane
  8. customgave impure material
  9. washFurther chromatography on silica, eluting with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-fdea489e5fdc41e982c01a6f18e2c07f
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

Loading…