Triphenylphosphine → methyl 2-[(1-tert-butoxycarbonylpiperidin-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

HRID 1169344Notes

Reaction equation

HRID 1169344 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].O[C:35]1[CH:36]=[CH:37][C:38]2[CH2:44][CH2:43][CH2:42][C:41]([C:45]([O:47][CH3:48])=[O:46])=[CH:40][C:39]=2[CH:49]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][C:35]2[CH:36]=[CH:37][C:38]3[CH2:44][CH2:43][CH2:42][C:41]([C:45]([O:47][CH3:48])=[O:46])=[CH:40][C:39]=3[CH:49]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 22989944methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Product 1

HCID 22990206methyl 2-[(1-tert-butoxycarbonylpiperidin-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylateYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To triphenylphosphine (2361 mg, 9.00 mmol), 1-tert-butoxycarbonyl-4-hydroxypiperidine (1812 mg, 9.00 mmol) and methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (655 mg, 3.00 mmol) dissolved in THF (15 ml) was added at 0° C. a solution of diisopropyl azodicarboxylate (1.772 ml, 9.00 mmol) in THF (2 ml), and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography (silica gel: 70 g, ethyl acetate/hexane=1/9→1/7). The objective fractions were concentrated under reduced pressure to obtain methyl 2-[(1-tert-butoxycarbonylpiperidin-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (1270 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThe objective fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-d6c7cdc6195548d4a2ae59e046abeded
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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