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Sodium hydride → N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

HRID 1731685
Notes
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Reaction equation

HRID 1731685 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.CCOCC.S(O)(=O)(=O)C.[C:41]([NH:48][C:49]1([CH2:52]O)[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>C(#N)C.O1CCCC1>[C:41]([NH:48][C:49]1([CH2:52][O:9][CH:3]2[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]2([CH3:10])[CH3:1])[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 5516962,2,5,5-Tetramethylcyclopentan-1-olHCID 20092326Ethoxyethane;1,4,7,10,13,16-hexaoxacyclooctadecaneHCID 20165745N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate

Product 1

HCID 20165730N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2,2,5,5-Tetramethyl-1-cyclopentanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sodium hydride (60% dispersion in oil) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6- ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate is added with vigorous stirring over a 10 minute period. After completion of the reaction, as judged by thin layer chromatography, it is quenched with dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane.

Workup

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-fc2ab26bae4748f5ac9058042d4d93d0
Source dataset
uspto-grants-1986_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04622418

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes