Triphenylphosphine → HCID 23511702, compound

HRID 354292

Reaction equation

HRID 354292 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23]O)=[O:20])([CH3:17])([CH3:16])[CH3:15].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>[C:14]([O:18][C:19]([N:21]1[CH2:27][CH2:26][CH2:25][CH:22]1[CH2:23][O:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]=1[Cl:13])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 76856Methyl 3,5-dichloro-4-hydroxybenzoateHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 23511702HCID 23511702, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3,5-dichloro-4-hydroxybenzoate (600 mg, 2.714 mmol), N-tert-butoxycarbonylprolinol (546 mg, 2.714 mmol), and Ph3P (854 mg, 3.257 mmol) in THF (10 mL) was added dropwise DIAD (0.68 mL, 3.283 mmol) at room temp and the mixture was stirred for 3 days at room temp, and for 18 hr at 70° C. The reaction mixture was concentrated and the residue was chromatographed on silica-gel with n-hexane-EtOAc (6:1, v/v) as eluent to give 988.8 mg (90%) methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3,5-dichlorobenzoate a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ1.44 (s, 9H), 1.88-2.15 (br m, 3H), 2.34 (br s, 1H), 3.40-3.44 (m, 2H), 3.92 (s, 3H), 3.92, 4.14 (m, 1H), 4.18 (br s, 2H), 7.98 (s, 2H); MS (FAB) m/z 404 (M++1).

Workup

  1. waitfor 18 hr at 70° C
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed on silica-gel with n-hexane-EtOAc (6:1

Sources & evidence

ORD record
ord-05b8615f1bb84faba0c8041a89ec1abb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Linked notes

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