Acetic Acid → HCID 24802847, compound

HRID 639858Notes

Reaction equation

HRID 639858 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:15][C@@:14]2([CH2:16][O:17][CH3:18])[CH2:13][NH:12][CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:19](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:15][C@@:14]2([CH2:16][O:17][CH3:18])[CH2:13][N:12]([CH3:19])[CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 24802841(1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo(4.1.0)heptane

Product 1

HCID 24802847HCID 24802847, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(1S,6R)-6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane (E2a, 25 mg) was dissolved in methanol (1 mL); acetic acid (0.015 mL) was added followed by sodium triacetoxyborohydride (27.8 mg) and formaldehyde 37% in water (0.06 mL). The reaction mixture was stirred at room temperature overnight. Volatiles were then evaporated and the residue partitioned between DCM (20 mL) and aqueous sat NaHCO3 (20 mL) solution, dried and concentrated. Purification by chromatography (NH column) eluting with a gradient 0-100% ethyl acetate-cyclohexane afforded the title compound (16 mg).

Workup

  1. customVolatiles were then evaporated
  2. customthe residue partitioned between DCM (20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customPurification by chromatography (NH column)
  6. washeluting with a gradient 0-100% ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-f56c5aa78c2142f2bbd63de736f498d0
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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