Triphenylphosphine → HCID 69117471, compound

HRID 902361Notes

Reaction equation

HRID 902361 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]([Cl: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>>[ClH:15].[Cl:15][C:9]1[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[C:7]2[C:12]([CH2:13][CH2:14][C@H:5]([CH2:4][NH2:1])[O:6]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 86609140HCID 86609140, compound

Product 1

HCID 69117471HCID 69117471, compoundYield 90.7%

Procedure

Treatment of (2R)-2-(azidomethyl)-7-chloro-8-(2-chlorophenyl)chroman (1.5 g, 4.48 mmol) with polymer-bound triphenylphosphine (3 mmol/g, 1.94 g, 5.82 mmol) according to the procedure described for Example 69, Step 10 provided 0.70 g (45%) of ((2R)-7-chloro-8-(2-chlorophenyl)chroman-2-yl)methanamine hydrochloride as a white solid salt, mp 220–222° C.; MS (ESI) m/z 308.1 ([M+H]+); [α]D25=−26.4° (c=1% SOLN, MeOH).

Sources & evidence

ORD record
ord-b38984bda6e2483281a6491f70438f0a
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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