Water → HCID 18419728, compound
Reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.O.[C:11](=[O:14])([O-])[O-:12].[K+].[K+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.O1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:33]([O:12][C:11]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)=[O:14])[CH2:34][CH2:35][CH3:36]Participants
6
Procedure
Isonipecotic acid (6.42 g) was dissolved in a 4:1 mixture of tetrahydrofuran:water (100 ml), potassium carbonate (10.3 g) and di-tert-butyl dicarbonate (11.4 g) were added and stirred at room temperature over night. The tetrahydrofuran was removed in vacuo and the residue dispersed between water (100 ml) and ethyl acetate (100 ml), the aqueous phase was extracted with ethyl acetate (3×75 ml). The combined organics were washed with brine and dried (MgSO4). The solution was filtered, evaporated to dryness to afford a white solid of N-butoxycarbonylpiperidine-4-carboxylic acid(11.6 g).
Workup
- customThe tetrahydrofuran was removed in vacuo
- additionthe residue dispersed between water (100 ml) and ethyl acetate (100 ml)
- extractionthe aqueous phase was extracted with ethyl acetate (3×75 ml)
- washThe combined organics were washed with brine
- dry with materialdried (MgSO4)
- filtrationThe solution was filtered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-e0baf33a5c2c45938fa35846ebb2c703
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06458830B1
Reaction notes
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