Phenol → N-[(1R)-2-methyl-1-(phenoxymethyl)propyl]-4-(trifluoromethyl)aniline

HRID 1360392Notes

Reaction equation

[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH2:4][OH:5].[C:18]1(O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:1][CH:2]([CH3:17])[C@@H:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:8]=1)[CH2:4][O:5][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)-3-Methyl-2-{[4-(trifluoromethyl)phenyl]amino}butan-1-ol (50 mg, 0.201 mmol), which is the compound obtained in Step 1 of Example 2, phenol (19 mg) and triphenylphosphine (63 mg) were dissolved in tetrahydrofuran (1 mL), and after cooling to 0° C., diisopropyl azodicarboxylate (0.13 mL) was added dropwise. The mixture was stirred overnight at 50° C. and purified by purification step A to give the title compound (2.18 mg).

Workup

custompurified by purification step A

Sources & evidence

ORD record: ord-5664b5bc77c349a9aa7539638b57d93d
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879863B2

Reaction notes

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