Triphenylphosphine → HCID 69116749, compound

HRID 902387Notes

Reaction equation

HRID 902387 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[Cl: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:23][C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[C:8]1[C:9]([F:15])=[CH:10][CH:11]=[C:12]2[C:7]=1[O:6][C@@H:5]([CH2:4][NH2:1])[CH2:14][CH2:13]2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609152HCID 86609152, compound

Product 1

HCID 69116749HCID 69116749, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of (2R)-2-(azidomethyl)-8-(2,4-dichlorophenyl)-7-fluorochroman (0.22 g, 0.62 mmol) with polymer-bound triphenylphosphine (3 mmol/g, 0.35 g, 1.05 mmol) in THF (10 mL) and water (0.5 mL) according to the procedure described for Example 69, Step 10 provided 97 mg (43%) of ((2R)-8-(2,4-dichlorophenyl)-7-fluorochroman-2-yl)methanamine hydrochloride as a white solid salt, mp 164–166° C.; MS (ESI) m/z 326.0 ([M+H]+); [α]D25=−26.00° (c=1% SOLN, MeOH).

Sources & evidence

ORD record
ord-e9851359efe0481bbf3e3f063ad09b28
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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