Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylate → Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

HRID 1663046Notes

Reaction equation

HRID 1663046 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([OH:19])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:19][C:6]1([CH2:5][CH2:4][OH:3])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 10469302Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21936021Tert-butyl 4-hydroxy-4-(2-hydroxyethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 31.20 g (108.50 mmol) of tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxy-1-piperidinecarboxylate (WO 02/16352) in 150 ml of tetrahydrofuran is added dropwise to a suspension of 4.12 g (108.50 mmol) of lithium aluminium hydride in 150 ml of tetrahydrofuran. The mixture is stirred at room temperature for 2 hours and is then worked up as described in Example 2 (step 2.4).

Sources & evidence

ORD record
ord-fa0e3695e6d34b7e8fcaa61e2f286ef4
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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