Triphenylphosphine → HCID 118114392, compound

HRID 1050505Notes

Reaction equation

HRID 1050505 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([F:14])[CH:13]=2)[C:10]([OH:15])=[N:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[C:16]([N:23]1[CH2:28][CH2:27][CH2:26][C@H:25]([OH:29])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([F:14])[CH:13]=2)[C:10](=[O:15])[N:9]([C@@H:27]2[CH2:26][CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28]2)[CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[CH:1]1([C:4]2[CH:5]=[C:6]3[C:11](=[C:12]([F:14])[CH:13]=2)[C:10]([O:29][C@@H:25]2[CH2:26][CH2:27][CH2:28][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24]2)=[N:9][CH:8]=[CH:7]3)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 178517613HCID 178517613, compound

Product 2

HCID 118114392HCID 118114392, compoundHCID 118115106HCID 118115106, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-cyclopropyl-8-fluoroisoquinolin-1-ol (500 mg, 2.46 mmol), (S)-1-BOC-3-hydroxypiperidine (1.49 g, 7.39 mmol), Ph3P (2.58 g, 9.84 mmol) in THF (20 mL) was stirred at RT into a clear solution. DIAD (1.94 mL, 9.84 mmol) was added dropwise. The mixture was stirred at RT for 48 h. The mixture was diluted with EtOAc, washed with water ×3, dried, and concentrated in vacuo. The residue was subjected to flash column chromatography with 0% to 5% EtOAc in DCM to afford (R)-tert-butyl 3-(6-cyclopropyl-8-fluoro-1-oxoisoquinolin-2(1H)-yl)piperidine-1-carboxylate (57) as minor product and (R)-tert-butyl 3-(6-cyclopropyl-8-fluoroisoquinolin-1-yloxy)piperidine-1-carboxylate as major product (58).

Workup

  1. stirringThe mixture was stirred at RT for 48 h
  2. washwashed with water ×3
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f97a8ee0d63349798eb4d9177c2c0097
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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