Aluminium lithium hydride → Tert-butyl 5-(hydroxymethyl)-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate
Reaction equation
[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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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%).
Workup
- customA 50 mL RB flask fitted with magnetic stirrer
- customAfter completion of the reaction (reaction was monitored by TLC), reaction mixture
- customwas quenched with ethyl acetate
- washwashed with water
- washThe organic layer was washed with brine solution
- dry with materialFinally the organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customto give crude Intermediate-15
Sources & evidence
- ORD record
- ord-cda9e7b51cbc4fbf955ce60dd53d3db5
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303016B2
Reaction notes
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