Sodium borohydride → 7-[2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester

HRID 2052900ノート

反応式

HRID 2052900 の反応式
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:17]([CH2:18][CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][CH2:14][C:13]1=[O:27]>CO.C(Cl)Cl>[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 100218997-[2-Oxo-6-(3-oxooctyl)-piperidin-1-yl]-heptanoic acid methyl ester

生成物 1

HCID 100446137-[2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester収率 61%

試薬・触媒・溶媒 2

HCID 887Methanol触媒HCID 6344Dichloromethane溶媒

実験手順

Sodium borohydride (24 mg, 0.63 mmol), followed by MeOH (2 drops), was added to a solution of 7-[2-oxo-6-(3-oxo-octyl)-piperidin-1-yl]-heptanoic acid methyl ester (23 mg, 0.063 mmol) in CH2Cl2 (1.0 mL) at 0° C. The mixture was allowed to warm to rt. After 4 h at rt, the reaction was quenched with HCl (11.0M aqueous) and extracted with EtOAc (3×10 mL). The combined organic phase was washed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL) then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 14 mg (61%) of the title compound.

後処理

  1. customthe reaction was quenched with HCl (11.0M aqueous)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic phase was washed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL)
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)

出典と根拠

ORDレコード
ord-67fe7773134c41debb65002de76f75bb
出典データセット
uspto-grants-2008_02
特許番号
US07326716B2

反応ノート

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