Acetic Acid → HCID 24802847, 화합물

HRID 639858노트

반응식

HRID 639858 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 24802847HCID 24802847, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-f56c5aa78c2142f2bbd63de736f498d0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691893B2

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