Methanol → tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate

HRID 246130ノート

反応式

HRID 246130 の反応式
[BH4-].[Li+].C([O:5][C:6](=O)[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:9][C:10](OCC)=[O:11])C.CO.O>C1COCC1.C(OCC)(=O)C>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:7]([CH2:6][OH:5])[CH2:8][CH2:9][CH2:10][OH:11])([CH3:22])([CH3:20])[CH3:21]

参加物

7

反応物 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 14420344(S)-Diethyl 2-(tert-butoxycarbonylamino)pentanedioate

生成物 1

HCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate収率 83%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Lithium borohydride (2.0 M in THF, 4.12 ml, 8.24 mmol) was cooled in an ice bath and a solution of (S)-2-tert-butoxycarbonylamino-pentanedioic acid diethyl ester (0.5 g, 1.65 mmol) in THF (5.5 ml) was added dropwise. The reaction was warmed to room temperature and stirred 16 h. Methanol was added very slowly to the reaction mixture. After a delayed, vigorous gas evolution had subsided, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate five times, and the combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to give 0.3 g (83%) of ((S)-4-hydroxy-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester. (M+Na)+=242.

後処理

  1. extractionThe aqueous layer was extracted with ethyl acetate five times
  2. washthe combined organic layers were washed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation
  5. customthe residue was purified by silica gel chromatography (methanol/dichloromethane)

出典と根拠

ORDレコード
ord-3126df2b95d14a2fa972e9a1c14753c6
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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