Borane;tetrahydrofuran → HCID 10664892, compound

HRID 1510201Notes

Reaction equation

[C:1]1([CH:7]([NH:9][C:10]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1COCC1>>[C:1]1([CH:7]([NH:9][CH2:10][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 11792457HCID 11792457, compound

Product 1

HCID 10664892HCID 10664892, compoundYield 95%

Procedure

Compound 4-[(1-phenylethyl)aminocarbonyl]methyl-1-[(4-fluorophenyl)methyl]piperidine (0.33 g, 0.93 mmol) was reacted with 1M BH3/THF (5.0 ml) to produce a viscous oil, 0.23 g (95% yield)(procedure E). 1H NMR (CD3Cl) δ 7.34-=7.21 (5H, m, Ar—H), 7.01-6.95 (2H, t, J=8.4 Hz, Ar—H), 4.09-4.07 (1H, d, J=6.0 Hz, NH), 3.77-3.71 (1H, q, J=6.3 Hz, PhCHMe), 3.42 (2H, s, p-FPhCH2), 2.82-2.78 (2H, d, J=10.8 Hz, N(CH)2), 2.55-2.37 (2H, m, NCH2), 1.91-1.83 (2H, t, J=11.4 Hz, N(CH)2), 1.59-1.53 (4H, m), 1.44-1.38 (1H, m), 1.36-1.34 (3H, d, J=6.0 Hz, CH3), 1.25-1.14 (2H, m), The free base was converted into its oxalate salt, m.p.=172-173° C. Anal. [C22H29FN2.2(COOH)2] Calculated: C, 59.99; H, 6.39; N, 5.38; Found C, 59.84; H, 6.46; N, 5.29.

Workup

customto produce a viscous oil, 0.23 g (95% yield)(procedure E)

Sources & evidence

ORD record: ord-1d5ce3f88f9b4a69bc1c2ddd627f8cef
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211916B2

Reaction notes

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