Acetic Acid → [(4,4-Dimethyl cyclohexyl)methyl](phenylmethyl)amine

HRID 70267노트

반응식

HRID 70267 반응식
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([CH:8]=O)[CH2:4][CH2:3]1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH:5]([CH2:8][NH:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 222352954,4-Dimethylcyclohexane-1-carbaldehyde

생성물 1

HCID 59474634[(4,4-Dimethyl cyclohexyl)methyl](phenylmethyl)amine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 4,4-dimethylcyclohexanecarbaldehyde (6.6 g, 0.047 mol), benzylamine (5.0 g, 0.047 mol) and acetic acid (1 mL) in methanol (60 mL) was stirred for 30 min at room temperature. Sodium triacetoxyborohydride (10.0 g, 0.047 mol) was added in one portion and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. The organic phase was washed with brine, silica gel was added and the mixture was concentrated in vacuo. The residue was purified by flash chromatography (CH2Cl2/MeOH), affording [(4,4-dimethyl cyclohexyl)methyl](phenylmethyl)amine as a white solid. (M+H) 232, 1.76 min. (LC/MS method B).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between dichloromethane and water
  3. washThe organic phase was washed with brine, silica gel
  4. additionwas added
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-347ca6a6b3f54dfc8cd6ef398b5e3de9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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