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

HRID 1419064

反応式

HRID 1419064 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c51709c944854e20a4de4b585ef90007
出典データセット
uspto-grants-1999_03
特許番号
US05885979

関連ノート

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