Triphenylphosphine → 4-(1-Oxo-1,2,3,4-tetrahydro-2,4a,5-triaza-fluoren-7-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2105434Notes

Reaction equation

HRID 2105434 reaction equation
[OH:1][C:2]1[CH:14]=[C:13]2[C:5]([N:6]3[C:11](=[CH:12]2)[C:10](=[O:15])[NH:9][CH2:8][CH2:7]3)=[N:4][CH:3]=1.O[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([O:1][C:2]2[CH:14]=[C:13]3[C:5]([N:6]4[C:11](=[CH:12]3)[C:10](=[O:15])[NH:9][CH2:8][CH2:7]4)=[N:4][CH:3]=2)[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 684640317-hydroxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one

Product 1

HCID 684647274-(1-Oxo-1,2,3,4-tetrahydro-2,4a,5-triaza-fluoren-7-yloxy)-piperidine-1-carboxylic acid tert-butyl esterYield 70%

Procedure

The title compound was synthesized in analogy to example 1, from 7-hydroxy-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one (example 84, intermediate a)), tert-butyl 4-hydroxy-1-piperidinecarboxylate (commercially available), triphenylphosphine and di-tert-butylazodicarboxylate, to give the desired product as a light brown solid (70%).

Sources & evidence

ORD record
ord-40f83609e58346439333069c4fb7dc61
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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