4-Benzyl-6-[(4-fluoro-3-methylphenoxy)methyl]-3-methyl-1,4-oxazepane → 6-[(4-Fluoro-3-methylphenoxy)methyl]-3-methyl-1,4-oxazepane

HRID 467489Notes

Reaction equation

C([N:8]1[CH2:14][CH:13]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[CH2:12][O:11][CH2:10][CH:9]1[CH3:25])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH:13]2[CH2:12][O:11][CH2:10][CH:9]([CH3:25])[NH:8][CH2:14]2)=[CH:18][C:19]=1[CH3:24]

Participants

Conditions

Temperature: 23 °C

Procedure

A suspension of 4-benzyl-6-[(4-fluoro-3-methylphenoxy)methyl]-3-methyl-1,4-oxazepane (4-6, 36 mg, 0.11 mmol) and Pearlman's catalyst (wet 20% Pd(OH)2/C, 100 mg) in methanol (20 mL) was stirred under a hydrogen balloon at 23° C. for 2 h. The mixture was filtered and the filtrate concentrated to give 6-[(4-fluoro-3-methylphenoxy)methyl]-3-methyl-1,4-oxazepane (4-7) as a ˜1:1 mixture of diastereomers (colorless oil). LRMS m/z (M+H) 254.3 found, 254.2 required.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate concentrated

Sources & evidence

ORD record: ord-1881a07eccea478eb024057d4abe284d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623863B2

Reaction notes

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