Triphenylphosphine → HCID 22100848, compound

HRID 1458407Notes

Reaction equation

HRID 1458407 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[C:24]2[CH:25]=[C:26]([OH:29])[CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH:30]([CH3:32])[CH3:31])=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43](O)[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:13]([O:17][C:18]([N:20]1[C:24]2[CH:25]=[C:26]([O:29][CH:43]3[CH2:44][CH2:45][N:40]([C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:39])[CH2:41][CH2:42]3)[CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH:30]([CH3:32])[CH3:31])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 221008391,1-Dimethylethyl 6-hydroxy-2-(1-methylethyl)-1H-benzimidazole-1-carboxylate

Product 1

HCID 22100848HCID 22100848, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.60 mL, 3.80 mmol) was added to a solution of 1-tert-butoxycarbonyl-6-hydroxy-2-isopropylbenzimidazole (690 mg, 2.30 mmol), 1-tert-butoxycarbonyl-4-hydroxypiperidine (925 mg, 4.60 mmol), triphenylphosphine (904 mg, 3.45 mmol) and THF (5 mL) at 25° C. After stirring for 12 hours, the solvent was removed in vacuo. Chromatography (SiO2, 100 g) of the resulting oil with hexane/ethyl acetate (1:1) afforded 1-tert-butoxycarbonyl-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-2-isopropylbenzimidazole.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ebbb59d0ec947c9a5d70b7f7449582a
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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