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

HRID 1182120

반응식

HRID 1182120 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-21cdab5396d74da699493784cc7af339
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288537B2

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