Aluminium lithium hydride → Tert-butyl 5-(hydroxymethyl)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate

HRID 623987ノート

反応式

HRID 623987 の反応式
[CH:1]12[CH2:10][C:5]3([C:11](OC)=[O:12])[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[N:2]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:12][CH2:11][C:5]12[CH2:4][CH:3]3[CH2:9][CH:7]([CH2:8][CH:1]([N:2]3[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)[CH2:6]2

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 897205112-Tert-butyl 5-methyl 2-azatricyclo[3.3.1.13,7]decane-2,5-dicarboxylate

生成物 1

HCID 89720512Tert-butyl 5-(hydroxymethyl)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A 50 mL RB flask fitted with magnetic stirrer was charged with 5 mL of THF, 2-tert-butyl 5-methyl 2-azatricyclo[3.3.1.13,7]decane-2,5-dicarboxylate, Intermediate-9 (0.15 g, 0.5 mmol) and cooled to 0° C. Under N2 atm, LAH was added portion wise (30 mg, 0.8 mmol) and stirred for 2 hr. After completion of the reaction (reaction was monitored by TLC), reaction mixture was quenched with ethyl acetate and washed with water followed by 1N HCl solution. The organic layer was washed with brine solution. Finally the organic layer was dried over anhydrous sodium sulfate and concentrated to give crude Intermediate-15, as an oily mass (0.12 g, yield=88%).

後処理

  1. customA 50 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction was monitored by TLC), reaction mixture
  3. customwas quenched with ethyl acetate
  4. washwashed with water
  5. washThe organic layer was washed with brine solution
  6. dry with materialFinally the organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give crude Intermediate-15

出典と根拠

ORDレコード
ord-cda9e7b51cbc4fbf955ce60dd53d3db5
出典データセット
uspto-grants-2016_04
特許番号
US09303016B2

反応ノート

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