Triphenylphosphine → HCID 66629630, compound

HRID 555381Notes

Reaction equation

HRID 555381 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:8]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([Si:44]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[O:45][CH:46]1[CH2:51][CH2:50][CH:49](O)[CH2:48][CH2:47]1)([CH3:43])([CH3:42])[CH3:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CN(C=O)C>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH:49]3[CH2:48][CH2:47][CH:46]([O:45][Si:44]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)[CH2:51][CH2:50]3)=[CH:17][CH:18]=1)[CH2:8]2

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 15632834130745-64-1HCID 66630625HCID 66630625, compound

Product 1

HCID 66629630HCID 66629630, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-adamantan-2-yl-4-hydroxy-benzamide (4 g, 14.74 mmol) in dry THF (100 mL) and DMF (75 mL) was added triphenyl phosphine (5.8 g, 22.11 mmol) and 4-(t-butyl-diphenyl-silanyloxy)-cyclohexanol (6.27 g, 17.69 mmol). The reaction mixture was cooled to 0° C. and DEAD (3.48 mL, 22.11 mmol) was added dropwise from an addition funnel over a period of 30 min. The reaction was gradually brought to room temperature and stirring continued for 16 hrs. The solvent was removed under vacuum and ether (100 mL) was added and cooled to 0° C. The solid formed was filtered off and the clear filtrate concentrated and purified by column chromatography using DCM as solvent to give 4.73 g (53%) of N-adamantan-2-yl-4-[4-(t-butyl-diphenyl-silanyloxy)-cyclohexyloxy]-benzamide as an oil.

Workup

  1. customwas gradually brought to room temperature
  2. customThe solvent was removed under vacuum and ether (100 mL)
  3. additionwas added
  4. temperaturecooled to 0° C
  5. customThe solid formed
  6. filtrationwas filtered off
  7. concentrationthe clear filtrate concentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-97c4ec863f3c445e86f43632e72276e0
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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