Triphenylphosphine → ((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methanamine hydrochloride

HRID 902369Notes

Reaction equation

HRID 902369 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][CH:19]=[CH:18][C:17]=3[Cl:22])[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:17]1[CH:18]=[CH:19][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 86609144(2R)-2-(azidomethyl)-8-(2-chlorophenyl)-7-fluorochroman

Product 1

HCID 69117669((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methanamine hydrochlorideYield 134.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of (2R)-2-(azidomethyl)-8-(2-chlorophenyl)-7-fluorochroman (0.33 g, 1.04 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 0.23 g (70%) of ((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methanamine hydrochloride as a white salt, mp 223–225° C.; MS (APPI) m/z 292 ([M+H]+); [α]D25=−40.00° (c=1% SOLN, MeOH).

Sources & evidence

ORD record
ord-931d214b77584526b67e1e20383b1efa
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…