Carbamate → (Quinolin-3-yl)methanol

HRID 539506

反応式

HRID 539506 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:11](=O)([O-:13])N.[BH4-].[Na+]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:13])[CH:2]=1

参加物

5

反応物 3

HCID 276Carbamate2 回HCID 7047Quinoline2 回HCID 4311764Sodium borohydride

生成物 1

HCID 12662983(Quinolin-3-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Synthesis of compounds ERW1041A, B, C, D, E, and 1069 were synthesized using the methods of Choi et al. Chemistry & Biology, Volume 12, Issue 4, Pages 469-475, except the amino-acid amines are protected by a quinoline-containing carbamate. This quinoline-containing carbamate is synthesized by reducing 3-quinolylcarbaldehyde with sodium borohydride in THF followed by an aqueous workup and flash chromatography yielding 3-quinolylcarbinol. para-Nitro-phenylchloroformate is reacted with 3-quinolylcarbinol in methylene chloride and N-methyl morpholine to give a carbonate of 3-quinoline methanol and para-Nitro-phenol. After purification by flash chromatography, this carbonate is reacted with the methyl ester of the amino acid in neat DMF to give the named compounds.

後処理

  1. customSynthesis of compounds ERW1041A, B, C, D, E, and 1069
  2. customwere synthesized
  3. customis synthesized

出典と根拠

ORDレコード
ord-081ecec58c714981b4aae8a58db36932
出典データセット
uspto-grants-2014_10
特許番号
US08871718B2

関連ノート

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