Toluene → HCID 117925141, compound

HRID 705715Notes

Reaction equation

HRID 705715 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15]O)[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 1140TolueneHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 89872603tert-Butyl (1R,3S,6S)-3-(hydroxymethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

Product 1

HCID 117925141HCID 117925141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of D7 (10 g, 44 mmol), phtalimide (10.29 g, 70 mmol) and triphenylphosphine (18.34 g, 70 mmol) in THF (150 mL) was cooled at 0° C., then a 40% solution of DEAD in toluene (31.94 mL, 70 mmol) was added. The mixture was stirred at room temperature for 3 hours, then water was added and the mixture was concentrated under vacuum; the residue was dissolved in DCM, washed with water and organics were evaporated. Cyclohexane (300 mL) and DCM (10 mL) were added, the precipitate was discarded and the filtrate was concentrated. The crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30) to give the title compound as a white solid. Yield (11 g, 71%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. customorganics were evaporated
  5. additionCyclohexane (300 mL) and DCM (10 mL) were added
  6. concentrationthe filtrate was concentrated
  7. customThe crude mixture was purified by silica gel column chromatography (cyclohexane/ethyl acetate=95:5 to 70/30)

Sources & evidence

ORD record
ord-27cb8e22c66545bcac440d3da6d74273
Source dataset
uspto-grants-2015_11
Patent number
US09174977B2

Reaction notes

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