Triphenylphosphine → 1-(tert-Butoxycarbonyl)-2'-benzyl-5',6'-dihydrospiro[piperidine-4,4'-[4H]pyrrolo[1,2-b]pyrazole]

HRID 8775Notes

Reaction equation

HRID 8775 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:26][CH2:27]O)([C:14]2[NH:18][N:17]=[C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:14]3[N:18]([N:17]=[C:16]([CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=3)[CH2:27][CH2:26]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178419060HCID 178419060, compound

Product 1

HCID 219838801-(tert-Butoxycarbonyl)-2'-benzyl-5',6'-dihydrospiro[piperidine-4,4'-[4H]pyrrolo[1,2-b]pyrazole]Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyeth-1-yl)-4-(3-benzyl-(1H)-pyrazol-5-yl)piperidine (125 mg, 0.32 mmol) from Step I in THF (4 mL) at 0° C. was added triphenylphosphine (85 mg, 0.32 mmol) and DEAD (0.051 mL, 0.32 mmol). The reaction was stirred for 20 min and was then allowed to warm to room temperature for 2 h. The mixture was concentrated and purified by flash chromatography eluting with 80% ethyl acetate in hexanes, then 5% methanol in methylene chloride to afford the title compound (100 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography
  3. washeluting with 80% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-23fa4558efeb46a98b4c522d23affa0c
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Reaction notes

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