Triphenylphosphine → HCID 69117450, compound

HRID 902378Notes

Reaction equation

HRID 902378 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[CH3:23])[C:9]([F:15])=[CH:10][CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[ClH:22].[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:9]([F:15])=[CH:10][CH:11]=[C:12]3[C:7]=2[O:6][C@@H:5]([CH2:4][NH2:1])[CH2:14][CH2:13]3)=[C:17]([CH3:23])[CH:18]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609148HCID 86609148, compound

Product 1

HCID 69117450HCID 69117450, compoundYield 136.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of (2R)-2-(azidomethyl)-8-(4-chloro-2-methylphenyl)-7-fluorochroman (0.30 g, 0.90 mmol) with polymer-bound triphenylphosphine (3 mmol/g, 0.5 g, 1.50 mmol) in THF (10 mL) and water (0.5 mL) according to the procedure described for Example 69, Step 10 provided 0.21 g (69%) of ((2R)-8-(4-chloro-2-methylphenyl)-7-fluorochroman-2-yl)methanamine hydrochloride as a white solid salt, mp 100–102° C.; MS (ESI) m/z 306.1 ([M+H]+).

Sources & evidence

ORD record
ord-cded4938b53440de95a913e770048e4d
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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