Triphenylphosphine → HCID 19010533, compound

HRID 1741733Notes

Reaction equation

HRID 1741733 reaction equation
O[CH:2]([CH3:30])[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:19][N:18]=1)[CH2:9][CH2:8]2.[O:31]([C:38]([NH:40][O:41][C:42]([O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:43])=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:31]([C:38]([N:40]([O:41][C:42]([O:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:43])[CH:2]([CH3:30])[C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)=[CH:19][N:18]=1)[CH2:9][CH2:8]2)=[O:39])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamineHCID 19010539HCID 19010539, compound

Product 1

HCID 19010533HCID 19010533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (0° C.) solution of 6-[3-hydroxy-1-butyn-1-yl]-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline (510 mg, 1.3 mmol), N,O-bis(phenoxycarbonyl)hydroxylamine (390 mg, 1.4 mmol), and triphenylphosphine (0.42 g, 1.6 mmol) in THF (10 mL) is added a solution of diisopropyl azodicarboxylate (320 mg, 0.32 mL, 1.6 mmol) in THF (2 mL). After 16 hours, the reaction is concentrated in vacuo and the residue chromatographed (silica gel. 1:1 EtOAc/hexanes) to afford 6-{3-[N,O-bis(phenoxycarbonyl)hydroxylamino]-1-butyn-1-yl}-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline as an oil.

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. customthe residue chromatographed (silica gel. 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-eae75f908c82463191e59a91aeccc411
Source dataset
uspto-grants-1994_08
Patent number
US05334600

Reaction notes

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