Citric Acid → Cyclohexyl-(3-hydroxy-propyl)-carbamic acid tert-butyl ester

HRID 1070558ノート

反応式

HRID 1070558 の反応式
[C:1]([O:5][C:6]([N:8]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:9][CH2:10][C:11](OCC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:9][CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22397304HCID 22397304、化合物

生成物 1

HCID 22397310Cyclohexyl-(3-hydroxy-propyl)-carbamic acid tert-butyl ester収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of ethyl N-tert-butoxycarbonyl-3-cyclohexylamino-propanoate (2a, 2.18 9, 7.3 mmol) in tetrahydrofuran (20 mL) was added lithium aluminium hydride (1.0 M solution in tetrahydrofuran. 10 mL). The reaction mixture was stirred for 1 h, after which ethyl acetate (5 mL) was slowly added. Subsequently, aqueous citric acid (0.5 M, 50 mL) was added and the heterogeneous mixture was extracted with Et2O (2×100 mL). The organic layer was washed with aqueous sodium hydrogencarbonate (1 N, 25 mL). Drying over magnesium sulphate, concentration under reduced pressure and purification by silica gel chromatography (eluent: ethyl acetate/heptane, 3:7, v/v) provided 1.50 g (80%) of the title compound as a white foam. ESI-MS: 258.2 (M+H)+, 280.3 (M+Na)+, 202.2 (M+H—C4H8)+, 158.2 (M+H-Boc)+. Rf (silica gel; ethyl acetate/heptane, 1:4, v/v): 0.31.

後処理

  1. extractionthe heterogeneous mixture was extracted with Et2O (2×100 mL)
  2. washThe organic layer was washed with aqueous sodium hydrogencarbonate (1 N, 25 mL)
  3. dry with materialDrying over magnesium sulphate, concentration under reduced pressure and purification by silica gel chromatography (eluent: ethyl acetate/heptane, 3:7, v/v)

出典と根拠

ORDレコード
ord-5fb9763043eb42759d05bd7c51f3c67c
出典データセット
uspto-grants-2005_06
特許番号
US06903107B1

反応ノート

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