Tetrahydrofuran → tert-Butyl (S)-(4-hydroxy-1-methoxybutan-2-yl)carbamate

HRID 1182120

反応式

HRID 1182120 の反応式
C([O:8][C:9](=O)[CH2:10][C@H:11]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][O:13][CH3:14])C1C=CC=CC=1.[Li+].[BH4-].C1COCC1>C(OCC)C>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:11]([CH2:12][O:13][CH3:14])[CH2:10][CH2:9][OH:8])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 57976545(S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

生成物 1

HCID 53259998tert-Butyl (S)-(4-hydroxy-1-methoxybutan-2-yl)carbamate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of (S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester (10.4 g, 32.3 mmol) in dry diethylether (70 ml) cooled to 0° C. is treated slowly with a 2.0 M solution of LiBH4 in THF (32.2 ml, 64.4 mmol). The reaction mixture is allowed to warm to ambient temperature and then left to stir. After 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid and extracted with ether. The ether phase is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (elution with a gradient 3:7 to 6:4 ethylacetate/hexane) to afford ((S)-3-Hydroxy-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester as a clear oil. [M-BOC] 120.13

後処理

  1. waitleft
  2. customAfter 6 hours the reaction mixture is quenched slowly with 0.5 M aqueous solution of citric acid
  3. extractionextracted with ether
  4. dry with materialThe ether phase is dried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (
  7. washelution with a gradient 3:7 to 6:4 ethylacetate/hexane)

出典と根拠

ORDレコード
ord-21cdab5396d74da699493784cc7af339
出典データセット
uspto-grants-2007_10
特許番号
US07288537B2

関連ノート

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