Triphenylphosphine → (R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate

HRID 1050502Notes

Reaction equation

HRID 1050502 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][CH2:22][C@H:21](O)[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].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>[C:2]1([O:1][C@@H:23]2[CH2:22][CH2:21][CH2:20][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:24]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 178517620HCID 178517620, compound

Product 1

HCID 118114503(R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-hydroxyisoquinoline (1.00 g, 6.9 mmol), (S)-1-BOC-3-hydroxypiperidine (4.17 g, 20.7 mmol), Ph3P (7.23 g, 27.6 mmol) in THF (40 mL) was stirred at RT into a clear solution. DIAD (5.43 mL, 27.6 mmol) was added dropwise. The mixture was stirred at RT for 1 h and then at 50° C. for overnight. 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 15% EtOAc in DCM to afford (R)-tert-butyl 3-(isoquinolin-1-yloxy)piperidine-1-carboxylate (53).

Workup

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

Sources & evidence

ORD record
ord-44cedc3a07494322973daebb61f4e0eb
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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