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

HRID 623987노트

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HRID 623987 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-cda9e7b51cbc4fbf955ce60dd53d3db5
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303016B2

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