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Sodium Bicarbonate → tert-Butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

HRID 8769
Notes
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Reaction equation

HRID 8769 reaction equation
[CH:1]([C:3]1([CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:2].C[Li].[C:28](=O)(O)[O-].[Na+]>C1COCC1.CCOCC>[OH:2][CH:1]([C:3]1([CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:7][CH2:8]1)[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21983955tert-Butyl 4-formyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylateHCID 178418348HCID 178418348, compound2×

Product 1

HCID 21983937tert-Butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-formyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.3 g, 17 mmol) in THF (170 mL) at −70° C. was added 1.4M methyl lithium in ether (13.3 mL, 19 mmol). After 2 h, an additional amount of 1.4M methyl lithium in ether (2.5 mL) was added. After an additional 30 min, the reaction was poured into aq. sodium bicarbonate and extracted three times with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title product (6.6 g) which was used directly in the next step.

Workup

  1. waitAfter an additional 30 min
  2. extractionextracted three times with ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f72326cb43594b419689d372b0652184
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091211B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes