Hydrochloric Acid → tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamate

HRID 1978396ノート

反応式

HRID 1978396 の反応式
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][C:27](OCC)=[O:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994062Ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate

生成物 1

HCID 21993723tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamate収率 40.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisobutylaluminium hydride (1.5 M in toluene, 57.0 ml, 85.5 mmol) was added dropwise to a stirred solution of ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate (9.35 g, 31.9 mmol) in tetrahydrofuran (100 ml) at 0° C. and the mixture was stirred at room temperature for 24 hours. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (2:1) to give 3-(3-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (3.24 g, 40%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was successively washed with water saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-a7680fa71dee469eaa7ce71a5aa4a2e4
出典データセット
uspto-grants-2001_05
特許番号
US06235731B1

反応ノート

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