Acetic Acid → HCID 25072816, compound

HRID 1096494Notes

Reaction equation

HRID 1096494 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]4[CH2:19][NH:20][CH2:21][CH2:22][C:12]([C:13]=34)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:25](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>COCCOC>[CH3:25][N:20]1[CH2:21][CH2:22][C:12]2=[CH:11][N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:13]=32)[CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 25072815HCID 25072815, compound

Product 1

HCID 25072816HCID 25072816, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-(Phenylsulfonyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol, Example 15 (34.4 mg, 0.11 mmol) was dissolved in DME (2 mL) and added formaldehyde (37% Wt. solution in water, 0.1 mL, 1.1 mmol), acetic acid (0.05 mL, 0.7 mmol) and sodium triacetoxyborohydride (156 mg, 0.7 mmol). The reaction mixture was stirred at room temperature for 24 H. The reaction was quenched by adding 1 M NaOH (5 mL). Aqueous phase (pH about 14) was separated and was then extracted with DCM (3×5 mL). The combined organic phases was washed with water and brine, and dried with MgSO4. The solvent was removed under vacuum. 20 mg pure product was obtained as an off-white solid. MS m/z 327 [M+H]+.

Workup

  1. customThe reaction was quenched
  2. additionby adding 1 M NaOH (5 mL)
  3. customAqueous phase (pH about 14) was separated
  4. extractionwas then extracted with DCM (3×5 mL)
  5. washThe combined organic phases was washed with water and brine
  6. dry with materialdried with MgSO4
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9d043d59ecb14a1f9638ab6ecb3e4818
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

Loading…