Acetic Acid → alpha-(4-Benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol

HRID 1419064

반응식

HRID 1419064 반응식
[NH2:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH:4]([OH:21])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]=1[O:19][CH3:20].[CH:27](=O)[C:28]([CH3:31])([CH3:30])[CH3:29].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]([OH:21])[C:3]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:2]=2[NH:1][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:6]([O:19][CH3:20])[CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 539319582-Amino-alpha-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol

생성물 1

HCID 54116645alpha-(4-Benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g), pivalaldehyde (3.35 ml), acetic acid (1.85 g) and ethanol (200 ml) was stirred for 30 min. To the mixture was added sodium cyanoborohydride (2.33 g) and the mixture was stirred for 24 h. After the mixture was concentrated in vacuo, the residue was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give α-(4-benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol (10.0 g) as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 24 h
  2. concentrationAfter the mixture was concentrated in vacuo
  3. additionthe residue was diluted with water (200 ml)
  4. extractionextracted with ethyl acetate (200 ml)
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-c51709c944854e20a4de4b585ef90007
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05885979

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