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Water → 3,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester

HRID 1912419
Notes
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Reaction equation

HRID 1912419 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][C:12]([NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])([C:16]([F:24])([F:23])[CH2:17]OS(C)(=O)=O)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][C:12]2([N:25]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])[CH2:17][C:16]2([F:24])[F:23])[CH2:11]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 582933543-Benzyloxycarbonylamino-3-(1,1-difluoro-2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 582933383,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl esterYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (1.7 g, with 40% mineral oil) in N,N-dimethylformamide (428 ml) cooled to 0° C. was added a solution of an optically-active compound of 3-benzyloxycarbonylamino-3-(1,1-difluoro-2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (17.1 g) in N,N-dimethylformamide (86 ml), and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The separated organic layer was sequentially washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to give the titled compound (12.6 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was sequentially washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-5ff145eff7ea4a6a8467e06774bfa630
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609647B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes