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Cyclopropylacetylene → (S)-2-amino-2'-(cyclopropylethynyl)-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

HRID 335768
Notes
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Reaction equation

HRID 335768 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1.[CH:22]1([C:25]#[CH:26])[CH2:24][CH2:23]1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16]([C:26]#[C:25][CH:22]3[CH2:24][CH2:23]3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 138823CyclopropylacetyleneHCID 58466172(R)-2-amino-2'-bromo-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Product 1

HCID 67240959(S)-2-amino-2'-(cyclopropylethynyl)-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418397
HCID 178418397, compound
Catalyst

Conditions

Temperature
50 °C

Procedure

A vial was charged with (R)-2-amino-2′-bromo-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (1.00 g, 2.88 mmol), cyclopropyl acetylene (0.732 mL, 8.64 mmol), copper(i) iodide (0.110 g, 0.576 mmol), and DIPA (14.40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.333 g, 0.288 mmol) was added, the vial was flushed with argon, and the reaction was heated to 50° C. and stirred overnight. The reaction was diluted with ethyl acetate and filtered through Celite. The solution was concentrated and purified via column chromatography (RediSep 40 g, gradient elution 0-10% MeOH:DCM) to afford (S)-2-amino-2′-(cyclopropylethynyl)-5H-spiro[oxazole-4,9′-xanthen]-7′-ol as a tan solid.

Workup

  1. customthe vial was flushed with argon
  2. additionThe reaction was diluted with ethyl acetate
  3. filtrationfiltered through Celite
  4. concentrationThe solution was concentrated
  5. custompurified via column chromatography (RediSep 40 g, gradient elution 0-10% MeOH:DCM)

Sources & evidence

ORD record
ord-043442d3252f45e7a43f67b5736814de
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883782B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes