Methyl Chloride → ((2r)-8-(Biphenyl-2-yl)-6-fluorochroman-2-yl)methanamine hydrochloride

HRID 902396Notes

Reaction equation

HRID 902396 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[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:47]C>C1COCC1.O>[ClH:47].[C:17]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:8]1[CH:9]=[C:10]([F:15])[CH:11]=[C:12]2[C:7]=1[O:6][C@@H:5]([CH2:4][NH2:1])[CH2:14][CH2:13]2

Participants

6

Reactant 3

HCID 6327Methyl ChlorideHCID 11776TriphenylphosphineHCID 86609156(2R)-2-(azidomethyl)-8-(biphenyl-2-yl)-6-fluorochroman

Product 1

HCID 69117682((2r)-8-(Biphenyl-2-yl)-6-fluorochroman-2-yl)methanamine hydrochlorideYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of (2R)-2-(azidomethyl)-8-(biphenyl-2-yl)-6-fluorochroman (0.85 g, 2.36 mmol) with polymer-bound triphenylphosphine (3 mmol/g, 1.02 g, 3.06 mmol) in THF (30 mL) and water (2 mL) according to the procedure described for Example Cl-Me provided 0.46 g (52%) of ((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methanamine hydrochloride as an off-white solid salt, mp 98° C.; MS (ESI) m/z 334.2 [M+H]+; [α]D25=−27.00° (c=1% SOLN, MeOH).

Sources & evidence

ORD record
ord-06431c76d5b0421d9ac53e652cb20128
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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