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Tributylphosphine → HCID 178454072, compound

HRID 271337
Notes
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Reaction equation

HRID 271337 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC.[F:47][C:48]([F:57])([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:49]O>C1(C)C=CC=CC=1.C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][CH2:49][C:48]([F:57])([F:47])[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13831Tributylphosphine2×HCID 730421,1'-(Azodicarbonyl)dipiperidine2×HCID 97938912,2-Difluoro-2-phenylethanolHCID 178418813HCID 178418813, compound

Product 1

HCID 178454072HCID 178454072, compound

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 0.23 g of g of cis-(4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester, 0.54 g of 1.1′-(azodicarbonyl)-dipiperidine and 20 mL of benzene was added 0.4 g of tri-n-butyl-phosphine and 1.3 g (8 equivalents) of 2,2-difluoro-2-phenyl-ethanol. The mixture was heated to 60° C. overnight, then an additional 0.5 g of 1.1′-(azodicarbonyl)-dipiperidine and 0.4 g of tri-n-butyl-phosphine was added and heating continued for another 24 h. The mixture was cooled, diluted with 25 mL of toluene, filtered and the filter pad washed with 5 mL of toluene. The filtrate was purified by chromatography on silica gel eluting with a gradient of 0%-20% ethyl acetate in hexane gave 0.15 g of product as a resin: 1H NMR (400 MHz, CDCl3) 7.5 (m, 5H), 3.95 (m, 2H), 3.4 (m, 1H), 1.95 (m, 2H), 1.6 (m, 6H), 1.45 (s, 9H).

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe filter pad washed with 5 mL of toluene
  5. customThe filtrate was purified by chromatography on silica gel eluting with a gradient of 0%-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e6ed7fbff69c4de0bd60b1cad2f4e5eb
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07452893B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes