Triphenylphosphine → 7-Benzyl-7-azabicyclo[4.1.0]heptane

HRID 23774Notes

Reaction equation

HRID 23774 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CCOCC>[CH2:1]([N:8]1[CH:14]2[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 117012502-(Benzylamino)cyclohexanol

Product 1

HCID 112176897-Benzyl-7-azabicyclo[4.1.0]heptaneYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclization of 2-Benzylamino-cyclohexanol. Diethyl azodicarboxylate (Aldrich, 95%, 3.6 ml, 22.6 mmol) was slowly added to an ether solution (50 ml) of 2-benzylaminio-cyclohexanol (3.1 g, 15 mmol) and PPh3 (5.94 g, 22.6 mmol) under N2, with stirring, in an ice-bath. After addition, the ice bath was removed, and the mixture stirred at room temperature for 36 h. The resulting crystalline precipitate was filtered and the solvent removed from the filtrate by rotary evaporation to yield the crude product, which was purified by column chromatography (petroleum ether: diethyl ether=50:50) (2.1 g, 75% yield).

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringthe mixture stirred at room temperature for 36 h
  4. filtrationThe resulting crystalline precipitate was filtered
  5. customthe solvent removed from the filtrate by rotary evaporation

Sources & evidence

ORD record
ord-7a1a690d70d6493fb83aeafb6b762f1a
Source dataset
uspto-grants-2005_02
Patent number
US06852865B2

Reaction notes

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